{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T13:52:11Z","timestamp":1791553931590,"version":"4.3.4"},"reference-count":91,"publisher":"American Chemical Society (ACS)","issue":"40","license":[{"start":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T00:00:00Z","timestamp":1790121600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T00:00:00Z","timestamp":1790121600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T00:00:00Z","timestamp":1790121600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/100016907","name":"Institute for the Promotion of Teaching Science and Technology","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100016907","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004156","name":"Mahidol University","doi-asserted-by":"publisher","award":["FF-077\/2568"],"award-info":[{"award-number":["FF-077\/2568"]}],"id":[{"id":"10.13039\/501100004156","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>This work discloses an alternative synthetic route to access benzofuro[2,3-b]quinolines. The reaction proceeds via Ag(I)-assisted cascade cyclization of 1-isocyano-2-((2-alkoxyphenyl)ethynyl)benzenes, derived from the corresponding N-(2-((2-alkoxyphenyl)ethynyl)phenyl)formamide derivatives, allowing a one-pot, two-step assembly of the benzofuroquinoline scaffolds with four fused rings. The salient features of the synthetic method are broad substrate scopes, good to excellent yields, and ease of experimental procedure. A gram-scale synthesis demonstrated the scalability and practical applicability of the present transformation. Mechanistic pathway of the current transformation was proposed based on control experiments and density functional calculations on the electronic structures. The photophysical properties and frontier molecular orbitals of some selected benzofuro[2,3-b]quinolines were evaluated using UV\u2013vis absorption and fluorescence spectroscopy and time-dependent density functional theory (TD-DFT) calculations.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01498","type":"journal-article","created":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T16:02:58Z","timestamp":1790179378000},"page":"13426-13437","source":"Crossref","is-referenced-by-count":0,"title":["Ag(I)-Promoted Cascade\nCyclization of 1-Isocyano-2-((2-alkoxyphenyl)ethynyl)benzenes\nto Access Benzofuro[2,3-\n                    <i>b<\/i>\n                    ]quinolines"],"prefix":"10.1021","volume":"91","author":[{"given":"Thanathip","family":"Chomphunuch","sequence":"first","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thikhamporn","family":"Uppalabat","sequence":"additional","affiliation":[{"name":"Department of Science Service (DSS) , 75\/7 Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Onnicha","family":"Khaikate","sequence":"additional","affiliation":[{"name":"King Mongkut\u2019s University of Technology North Bangkok , , ,","place":["Bangkok, Thailand, 10800"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thanaset","family":"Kititheerakul","sequence":"additional","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nattawoot","family":"Hassa","sequence":"additional","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0300-4205","authenticated-orcid":true,"given":"Panida","family":"Surawatanawong","sequence":"additional","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8745-2322","authenticated-orcid":true,"given":"Pawaret","family":"Leowanawat","sequence":"additional","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6865-2270","authenticated-orcid":true,"given":"Darunee","family":"Soorukram","sequence":"additional","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0743-1300","authenticated-orcid":true,"given":"Vichai","family":"Reutrakul","sequence":"additional","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5665-0254","authenticated-orcid":true,"given":"Thanthapatra","family":"Bunchuay","sequence":"additional","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4638-4356","authenticated-orcid":true,"given":"Chutima","family":"Kuhakarn","sequence":"additional","affiliation":[{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]},{"name":"Mahidol University , , Rama VI Road , ,","place":["Bangkok, Thailand, 10400"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,23]]},"reference":[{"key":"2026100909091000000_cit1a","doi-asserted-by":"crossref","DOI":"10.1002\/9781119998372","volume-title":"Heterocycles\nin Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry\nand Applications","author":"Pozharskii","year":"2011"},{"key":"2026100909091000000_cit1b","volume-title":"The Chemistry of Heterocycles: Structure, Reactions, Synthesis\nand Applications","author":"Eicher","year":"2013"},{"key":"2026100909091000000_cit1c","doi-asserted-by":"publisher","first-page":"3075","DOI":"10.1016\/j.tetlet.2014.11.046","article-title":"Nature Loves Nitrogen Heterocycles","volume":"56","author":"Walsh","year":"2015","journal-title":"Tetrahedron Lett."},{"key":"2026100909091000000_cit1d","doi-asserted-by":"publisher","first-page":"10109","DOI":"10.1021\/acs.joc.6b02034","article-title":"The Modern\nFace of Synthetic Heterocyclic Chemistry","volume":"81","author":"Cabrele","year":"2016","journal-title":"J.\nOrg. Chem."},{"key":"2026100909091000000_cit1e","doi-asserted-by":"publisher","first-page":"102211","DOI":"10.1016\/j.isci.2021.102211","article-title":"Pharmaceutically Relevant (Hetero)cyclic\nCompounds and Natural Products from Lignin-Derived Monomers: Present\nand Perspectives","volume":"24","author":"Afanasenko","year":"2021","journal-title":"iScience"},{"key":"2026100909091000000_cit1f","doi-asserted-by":"publisher","first-page":"6611","DOI":"10.1039\/C6OB00936K","article-title":"Modern Advances\nin Heterocyclic Chemistry in Drug Discovery","volume":"14","author":"Taylor","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"2026100909091000000_cit1g","doi-asserted-by":"publisher","first-page":"44247","DOI":"10.1039\/D0RA09198G","article-title":"Prescribed Drugs Containing Nitrogen\nHeterocycles: An Overview","volume":"10","author":"Heravi","year":"2020","journal-title":"RSC Adv."},{"key":"2026100909091000000_cit1h","volume-title":"The Organic Chemistry\nof Drug Design and Drug Action","author":"Silverman","year":"2014"},{"key":"2026100909091000000_cit1i","doi-asserted-by":"publisher","first-page":"5","DOI":"10.2174\/2215083805666190613125700","article-title":"Naturally\nAvailable Nitrogen-Containing Fused Heterocyclics as Prospective Lead\nMolecules in Medicinal Chemistry","volume":"7","author":"Bhardwaj","year":"2021","journal-title":"Curr. Tradit.\nMed."},{"key":"2026100909091000000_cit1j","doi-asserted-by":"publisher","first-page":"135240","DOI":"10.1016\/j.tet.2026.135240","article-title":"The Chemistry\nof Common Drug-Related Heterocycles. Part I \u2013 Aromatic Monocyclic\nSix-Membered Heterocycles Containing One or Two Nitrogen Atoms","volume":"195","author":"Barbosa","year":"2026","journal-title":"Tetrahedron"},{"key":"2026100909091000000_cit2a","doi-asserted-by":"publisher","first-page":"3810","DOI":"10.1002\/anie.201209479","article-title":"Large N-Heteroacenes:\nNew Tricks for Very Old Dogs","volume":"52","author":"Bunz","year":"2013","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026100909091000000_cit2b","doi-asserted-by":"publisher","first-page":"1676","DOI":"10.1021\/acs.accounts.5b00118","article-title":"The Larger Linear N-Heteroacenes","volume":"48","author":"Bunz","year":"2015","journal-title":"Acc. Chem. Res."},{"key":"2026100909091000000_cit2c","doi-asserted-by":"publisher","first-page":"2334","DOI":"10.1021\/acs.accounts.7b00275","article-title":"The Tetraarylpyrrolo[3,2-b]pyrroles\u2013From Serendipitous Discovery to Promising\nHeterocyclic Optoelectronic Materials","volume":"50","author":"Krzeszewski","year":"2017","journal-title":"Acc.\nChem. Res."},{"key":"2026100909091000000_cit2d","doi-asserted-by":"publisher","first-page":"1575","DOI":"10.1021\/acs.accounts.9b00160","article-title":"N-Heteroacenes and N-Heteroarenes as N-Nanocarbon Segments","volume":"52","author":"Bunz","year":"2019","journal-title":"Acc. Chem. Res."},{"key":"2026100909091000000_cit2e","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202200460","article-title":"Recent Advances\ntowards the Synthesis and Material Applications of Indoloindoles","volume":"17","author":"Paul","year":"2022","journal-title":"Chem. - Asian J."},{"key":"2026100909091000000_cit2f","doi-asserted-by":"publisher","first-page":"216500","DOI":"10.1016\/j.ccr.2025.216500","article-title":"Heterocyclic and Heteropolycyclic\nMoieties in Organic Hole Transport Materials for Perovskite Solar\nCells: Design, Synthesis, and Performance","volume":"532","author":"Afraj","year":"2025","journal-title":"Coord.\nChem. Rev."},{"key":"2026100909091000000_cit3a","doi-asserted-by":"publisher","first-page":"2983","DOI":"10.1039\/b707576f","article-title":"Synthesis, Structure\nand Stereochemistry\nof Quinoline Alkaloids from Choisya Ternata","volume":"5","author":"Boyd","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"2026100909091000000_cit3b","doi-asserted-by":"publisher","first-page":"1344","DOI":"10.1021\/np0000318","article-title":"Constituents of Boronia pinnata","volume":"63","author":"Ito","year":"2000","journal-title":"J. Nat. Prod."},{"key":"2026100909091000000_cit3c","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.jchromb.2013.10.025","article-title":"Pharmacokinetics, Tissue Distribution\nand Excretion Study of Dictamnine, A Major Bioactive Component from\nthe Root Bark of Dictamnus dasycarpus Turcz. (Rutaceae)","volume":"942\u2013943","author":"Wang","year":"2013","journal-title":"J. Chromatogr. B"},{"key":"2026100909091000000_cit3d","doi-asserted-by":"publisher","first-page":"114864","DOI":"10.1016\/j.bcp.2021.114864","article-title":"Dictamnine, a Novel\nc-Met Inhibitor, Suppresses the Proliferation of Lung Cancer Cells\nby Downregulating the PI3K\/AKT\/mTOR and MAPK Signaling Pathways","volume":"195","author":"Yu","year":"2022","journal-title":"Biochem. Pharmacol."},{"key":"2026100909091000000_cit3e","doi-asserted-by":"publisher","first-page":"136222","DOI":"10.1016\/j.molstruc.2023.136222","article-title":"Dictamnine Derivatives as a Novel Family of Dual Inhibitors\nfor Cholinesterase and \u03b2-Amyloid Aggregation","volume":"1293","author":"Zhao","year":"2023","journal-title":"J. Mol. Struct."},{"key":"2026100909091000000_cit3f","doi-asserted-by":"publisher","first-page":"2251","DOI":"10.1021\/jo01082a624","article-title":"Notes: Isolation of Evolitrine from Cusparia macrocarpa","volume":"25","author":"Rapoport","year":"1960","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit3g","doi-asserted-by":"crossref","first-page":"77","DOI":"10.3998\/ark.5550190.0006.207","article-title":"Isolation, Synthesis and Biological\nActivity of Evolitrine and Analogs","volume":"11","author":"Lal","year":"2005","journal-title":"ARKIVOC"},{"key":"2026100909091000000_cit3h","doi-asserted-by":"publisher","first-page":"995","DOI":"10.1021\/np000012y","article-title":"New Quinoline Alkaloids from Ruta chalepensis","volume":"63","author":"El Sayed","year":"2000","journal-title":"J. Nat. Prod."},{"key":"2026100909091000000_cit4a","doi-asserted-by":"publisher","first-page":"1295","DOI":"10.1021\/jm00126a025","article-title":"Synthesis and Antitumor Activity\nof Fused Tetracyclic Quinoline Derivatives. 1","volume":"32","author":"Yamato","year":"1989","journal-title":"J. Med. Chem."},{"key":"2026100909091000000_cit4b","doi-asserted-by":"publisher","first-page":"2040","DOI":"10.1021\/jm970044r","article-title":"Synthesis and Antitumor Properties of N-[2-(Dimethylamino)ethyl]carboxamide Derivatives of Fused Tetracyclic\nQuinolines and Quinoxalines: A New Class of Putative Topoisomerase\nInhibitors","volume":"40","author":"Deady","year":"1997","journal-title":"J. Med. Chem."},{"key":"2026100909091000000_cit4c","doi-asserted-by":"publisher","first-page":"6103","DOI":"10.1016\/j.bmcl.2012.08.032","article-title":"New Derivatives\nof 11-Methyl-6-[2-(dimethylamino)ethyl]-6H-indolo[2,3-b]quinoline as Cytotoxic DNA Topoisomerase II Inhibitors","volume":"22","author":"Luniewski","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"2026100909091000000_cit4d","doi-asserted-by":"publisher","first-page":"4820","DOI":"10.1016\/j.bmc.2012.05.054","article-title":"Synthesis\nand in Vitro Antiproliferative Activity of New 11-Aminoalkylamino-Substituted\n5H- and 6H-Indolo[2,3-b]quinolines; Structure-Activity Relationships of Neocryptolepines\nand 6-Methyl Congeners","volume":"20","author":"Wang","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"2026100909091000000_cit4e","doi-asserted-by":"publisher","first-page":"5187","DOI":"10.1021\/acsomega.7b00840","article-title":"Expedient\nSynthesis of Indolo[2,3-b]quinolines, Chromeno[2,3-b]indoles, and 3-Alkenyl-Oxindoles from 3,3\u2032-Diindolylmethanes\nand Evaluation of Their Antibiotic Activity Against Methicillin-Resistant Staphylococcus aureus","volume":"2","author":"Challa","year":"2017","journal-title":"ACS Omega"},{"key":"2026100909091000000_cit4f","doi-asserted-by":"publisher","first-page":"143","DOI":"10.1071\/CH99166","article-title":"Synthesis and Cytotoxic Activity\nof N-[2-(Dimethylamino)ethyl] Carboxamide Derivatives\nof Benzofuro[2,3-b]quinoline, 6H-Quinindoline, Indeno[2,1-b]quinoline and [1]Benzothieno[2,3-b]quinoline","volume":"53","author":"Bu","year":"2000","journal-title":"Aust. J. Chem."},{"key":"2026100909091000000_cit4g","doi-asserted-by":"publisher","first-page":"2462","DOI":"10.1016\/j.bmc.2005.11.036","article-title":"Synthesis and Biological Evaluation of Conformationally\nConstrained Analogs of the Antitumor Agents XK469 and SH80. Part 5","volume":"14","author":"Hazeldine","year":"2006","journal-title":"Bioorg. Med. Chem."},{"key":"2026100909091000000_cit4h","doi-asserted-by":"publisher","first-page":"602","DOI":"10.1016\/j.ejmech.2009.10.050","article-title":"Identification of Benzofuro[2,3-b]quinoline\nDerivatives as a New Class of Antituberculosis agents","volume":"45","author":"Yang","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"2026100909091000000_cit4i","doi-asserted-by":"publisher","first-page":"103347","DOI":"10.1016\/j.bioorg.2019.103347","article-title":"Functionalization of 9-Thioxanthone\nat the 1-Position: from Arylamino Derivatives to [1]Benzo(thio)pyrano[4,3,2-de]benzothieno[2,3-b]quinolines of Biological\nInterest","volume":"94","author":"Brikci-Nigassa","year":"2020","journal-title":"Bioorg. Chem."},{"key":"2026100909091000000_cit4j","doi-asserted-by":"publisher","first-page":"112391","DOI":"10.1016\/j.ejmech.2020.112391","article-title":"Targeting mTOR for Fighting Diseases: A Revisited Review\nof mTOR Inhibitors","volume":"199","author":"Xu","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"2026100909091000000_cit4k","doi-asserted-by":"publisher","first-page":"732","DOI":"10.1134\/S1070363222040156","article-title":"The New Antibacterial Agents Based\non the Fused Aromatic Heterocyclic Compounds: Design, Synthesis, and\nAntibacterial Activity","volume":"92","author":"Faramarzi","year":"2022","journal-title":"Russ. J. Gen. Chem."},{"key":"2026100909091000000_cit4l","doi-asserted-by":"publisher","first-page":"18703","DOI":"10.1021\/acs.jmedchem.5c01942","article-title":"Identification\nof Benzofuro[2,3-b]pyridine Pseudonatural Product\nas a Novel Class of Ferritinophagy Inhibitors that Potently Suppress\nFerroptosis","volume":"68","author":"Zhang","year":"2025","journal-title":"J. Med. Chem."},{"key":"2026100909091000000_cit4m","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.202400514","article-title":"Diversity\nOriented Strategy (DOS) for the Efficient Synthesis of Benzofuro[2,3-b]pyridine Derivatives with Anticancer Activity","volume":"20","author":"Ereje","year":"2025","journal-title":"ChemMedChem"},{"key":"2026100909091000000_cit4n","doi-asserted-by":"publisher","first-page":"118464","DOI":"10.1016\/j.ejmech.2025.118464","article-title":"Discovery of \u03b1-Carboline Fused Benzofuran-Containing Anticancer\nAgents as Rapid Apoptosis Inducers Through Intrinsic Pathway","volume":"303","author":"Lin","year":"2026","journal-title":"Eur. J. Med. Chem."},{"key":"2026100909091000000_cit5a","doi-asserted-by":"publisher","first-page":"97","DOI":"10.1016\/j.dyepig.2014.03.027","article-title":"Synthesis\nand Evaluation of New BODIPY-Benzofuroquinoline\nConjugates for Sensitive and Selective DNA Detection","volume":"107","author":"Du","year":"2014","journal-title":"Dyes Pigm."},{"key":"2026100909091000000_cit5b","doi-asserted-by":"publisher","first-page":"7397","DOI":"10.1021\/acs.chemrev.6b00176","article-title":"Molecular Design of Benzodithiophene-Based\nOrganic Photovoltaic Materials","volume":"116","author":"Yao","year":"2016","journal-title":"Chem. Rev."},{"key":"2026100909091000000_cit5c","doi-asserted-by":"publisher","first-page":"1236","DOI":"10.1021\/acs.orglett.7b00323","article-title":"Construction of Bisbenzofuro[2,3-b:3\u2032,2\u2032-e]pyridines by Palladium-Catalyzed\nDouble Intramolecular Oxidative C\u2013H\/C\u2013H Coupling","volume":"19","author":"Kaida","year":"2017","journal-title":"Org. Lett."},{"key":"2026100909091000000_cit5d","doi-asserted-by":"publisher","first-page":"7797","DOI":"10.1002\/er.6363","article-title":"Synthesis, Electrochemical, Photophysical, and Photovoltaic\nProperties of New Fluorescent Compounds: 3H-Benzofuro[2,3-b]pyrazolo[4,3-f]quinoline","volume":"45","author":"Ghamati","year":"2021","journal-title":"Int. J. Energy Res."},{"key":"2026100909091000000_cit5e","doi-asserted-by":"publisher","first-page":"440","DOI":"10.1134\/S1070428021030167","article-title":"Synthesis\nof 3H-[1]Benzofuro[2,3-b]imidazo[4,5-f]quinolines as New Fluorescent Heterocyclic Systems for\nDye-Sensitized Solar Cells","volume":"57","author":"Sadeghzadeh","year":"2021","journal-title":"Russ. J. Org. Chem."},{"key":"2026100909091000000_cit5f","doi-asserted-by":"publisher","first-page":"110584","DOI":"10.1016\/j.dyepig.2022.110584","article-title":"Benzofuro[2,3-c]isoquinolines as Novel\nAIEgens: Modulation of AIE Characteristics by a Single Methoxy group","volume":"206","author":"Kim","year":"2022","journal-title":"Dyes Pigm."},{"key":"2026100909091000000_cit5g","doi-asserted-by":"publisher","first-page":"112612","DOI":"10.1016\/j.dyepig.2024.112612","article-title":"Indole-, Benzofuran- and Benzothiophene-Containing\nAnalogues of Ceramidonines and Fused 3,9-Diazaperylenes: Synthesis\nand Physicochemical Properties of These New Polycyclic Azaarenes","volume":"235","author":"Mast","year":"2025","journal-title":"Dyes Pigm."},{"key":"2026100909091000000_cit5h","doi-asserted-by":"publisher","first-page":"31840","DOI":"10.1039\/D5RA05420F","article-title":"Metal-Free Synthesis of Tricyclic\nBenzofuro[2,3-c]pyridin-3-ol Derivatives, Characterization,\nand Photoluminescence Properties","volume":"15","author":"Saini","year":"2025","journal-title":"RSC Adv."},{"key":"2026100909091000000_cit6a","doi-asserted-by":"publisher","first-page":"487","DOI":"10.1002\/jhet.5570160315","article-title":"The Synthesis of Benzofuroquinolines.\nI. Some Benzofuro[2,3-b]quinoline and Benzofuro[3,2-c]quinoline Derivatives","volume":"16","author":"Kawase","year":"1979","journal-title":"J. Heterocycl.\nChem."},{"key":"2026100909091000000_cit6b","doi-asserted-by":"publisher","first-page":"1057","DOI":"10.1246\/bcsj.53.1057","article-title":"The Synthesis\nof Benzofuroquinolines. II. Two Benzofuroquinolinones and Some Benzofuroquinoline\nDerivatives","volume":"53","author":"Kawase","year":"1980","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"2026100909091000000_cit7","doi-asserted-by":"publisher","first-page":"98","DOI":"10.1021\/jacs.8b11466","article-title":"Cobalt-Catalyzed Electrophilic\nAminations with Anthranils: An Expedient Route to Condensed Quinolines","volume":"141","author":"Li","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"2026100909091000000_cit8a","doi-asserted-by":"publisher","first-page":"10866","DOI":"10.1039\/C8CC04264K","article-title":"Gold-Catalyzed Annulations of N-Aryl\nynamides with Benzisoxazoles to Construct 6H-Indolo[2,3-b]quinoline Cores","volume":"54","author":"Tsai","year":"2018","journal-title":"Chem. Commun."},{"key":"2026100909091000000_cit8b","doi-asserted-by":"publisher","first-page":"4452","DOI":"10.1039\/C9OB00468H","article-title":"Direct Access to Benzofuro[2,3-b]quinoline\nand 6H-Chromeno[3,4-b]quinoline\nCores through Gold-Catalyzed Annulation of Anthranils with Arenoxyethynes\nand Aryl Propargyl Ethers","volume":"17","author":"Patil","year":"2019","journal-title":"Org. Biomol. Chem."},{"key":"2026100909091000000_cit8c","doi-asserted-by":"publisher","first-page":"5640","DOI":"10.1021\/acs.orglett.0c01999","article-title":"Metal-Free, Visible-Light-Enabled\nDirect C3\u2013H Arylation of Anthranils","volume":"22","author":"Adak","year":"2020","journal-title":"Org. Lett."},{"key":"2026100909091000000_cit9","doi-asserted-by":"publisher","first-page":"153395","DOI":"10.1016\/j.tetlet.2021.153395","article-title":"Synthetic Studies towards Benzofuro[2,3-b]quinoline\nand 6H-Indolo[2,3-b]quinoline Cores:\nTotal Synthesis of Norneocryptolepine and Neocryptolepine","volume":"82","author":"Aksenov","year":"2021","journal-title":"Tetrahedron Lett."},{"key":"2026100909091000000_cit10a","doi-asserted-by":"publisher","first-page":"1785","DOI":"10.1016\/j.tet.2018.02.038","article-title":"2-Aminophenones, a\nCommon Precursor to N-Aryl Isatins and Acridines\nEndowed with Bioactivities","volume":"74","author":"Brikci-Nigassa","year":"2018","journal-title":"Tetrahedron"},{"key":"2026100909091000000_cit10b","doi-asserted-by":"publisher","first-page":"1271","DOI":"10.1055\/s-0040-1706542","article-title":"Iodothiophenes\nand Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines","volume":"53","author":"Bouarfa","year":"2021","journal-title":"Synthesis"},{"key":"2026100909091000000_cit11","doi-asserted-by":"publisher","first-page":"152808","DOI":"10.1016\/j.tetlet.2020.152808","article-title":"A Simple and\nEfficient Synthesis\nof Benzofuroquinolines via the Decarboxylative Cross-Coupling","volume":"66","author":"Rathod","year":"2021","journal-title":"Tetrahedron Lett."},{"key":"2026100909091000000_cit12a","doi-asserted-by":"publisher","first-page":"3127","DOI":"10.1021\/ja00086a054","article-title":"A Novel Tin-Mediated\nIndole Synthesis","volume":"116","author":"Fukuyama","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"2026100909091000000_cit12b","doi-asserted-by":"publisher","first-page":"1043","DOI":"10.1002\/jhet.5570350504","article-title":"Development of a Novel Indole Synthesis\nand Its Application to Natural Products Synthesis","volume":"35","author":"Kobayashi","year":"1998","journal-title":"J. Heterocycl. Chem."},{"key":"2026100909091000000_cit12c","doi-asserted-by":"publisher","first-page":"6325","DOI":"10.1016\/S0040-4039(99)01169-7","article-title":"an Isonitrile-Alkyne Cascade to Di-Substituted Indoles","volume":"40","author":"Rainier","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"2026100909091000000_cit12d","doi-asserted-by":"publisher","first-page":"1977","DOI":"10.1021\/ol991133w","article-title":"New Access to 2,3-Disubstituted Quinolines through Cyclization of o-Alkynylisocyanobenzenes","volume":"1","author":"Suginome","year":"1999","journal-title":"Org. Lett."},{"key":"2026100909091000000_cit12e","doi-asserted-by":"publisher","first-page":"6213","DOI":"10.1021\/jo000831n","article-title":"Cascades to Substituted Indoles","volume":"65","author":"Rainier","year":"2000","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit12f","doi-asserted-by":"publisher","first-page":"429","DOI":"10.1055\/s-2000-6354","article-title":"Synthesis of 2,3-Disubstituted Indoles by Palladium-Mediated\nCoupling of 2-Iodoindoles","volume":"2000","author":"Tokuyama","year":"2000","journal-title":"Synthesis"},{"key":"2026100909091000000_cit12g","doi-asserted-by":"publisher","first-page":"6715","DOI":"10.1016\/j.tetlet.2009.09.096","article-title":"Tetrabutylammonium Chloride-Triggered 6-endo Cyclization\nof o-Alkynylisocyanobenzenes: An Efficient Synthesis\nof 2-Chloro-3-Substituted Quinolines","volume":"50","author":"Liu","year":"2009","journal-title":"Tetrahedron\nLett."},{"key":"2026100909091000000_cit12h","doi-asserted-by":"publisher","first-page":"3422","DOI":"10.1021\/ol901267h","article-title":"(PhTe)2-Mediated\nIntramolecular Radical Cyclization of o-Ethynylaryl\nIsocyanides Leading to Bistellurated Quinolines upon Visible-Light\nIrradiation","volume":"11","author":"Mitamura","year":"2009","journal-title":"Org. Lett."},{"key":"2026100909091000000_cit12i","doi-asserted-by":"publisher","first-page":"822","DOI":"10.1246\/bcsj.20100044","article-title":"Synthesis of 2-Halogenated\nQuinolines by Halide-Mediated Intramolecular Cyclization of o-Alkynylaryl Isocyanides","volume":"83","author":"Mitamura","year":"2010","journal-title":"Bull. Chem.\nSoc. Jpn."},{"key":"2026100909091000000_cit12j","doi-asserted-by":"publisher","first-page":"7502","DOI":"10.1021\/jo1017525","article-title":"Synthesis of 2-Alkoxy(aroxy)-3-Substituted Quinolines by DABCO-Promoted\nCyclization of o-Alkynylaryl Isocyanides","volume":"75","author":"Zhao","year":"2010","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit12k","doi-asserted-by":"publisher","first-page":"3768","DOI":"10.1039\/C0OB01168A","article-title":"Photochemical Intramolecular Cyclization of o-Alkynylaryl\nIsocyanides with Organic Dichalcogenides Leading to 2,4-Bischalcogenated\nQuinolines","volume":"9","author":"Mitamura","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"2026100909091000000_cit12l","doi-asserted-by":"publisher","first-page":"1163","DOI":"10.1021\/jo1021772","article-title":"Synthesis of 2,4-Diiodoquinolines via the Photochemical Cyclization of o-Alkynylaryl\nIsocyanides with Iodine","volume":"76","author":"Mitamura","year":"2011","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit12m","doi-asserted-by":"publisher","first-page":"4270","DOI":"10.1021\/ol302035j","article-title":"Palladium-Catalyzed\nCascade Process Consisting of Isocyanide Insertion and Benzylic C(sp3)\u2013H Activation: Concise Synthesis of Indole Derivatives","volume":"14","author":"Nanjo","year":"2012","journal-title":"Org. Lett."},{"key":"2026100909091000000_cit12n","doi-asserted-by":"publisher","first-page":"3754","DOI":"10.1021\/ol4016699","article-title":"Synthesis\nof 3-Acyl-2-arylindole via Palladium-catalyzed Isocyanide\nInsertion and Oxypalladation of Alkyne","volume":"15","author":"Nanjo","year":"2013","journal-title":"Org.\nLett."},{"key":"2026100909091000000_cit12o","doi-asserted-by":"publisher","first-page":"652","DOI":"10.1021\/acs.joc.6b02668","article-title":"Synthesis of 1,2-Bis(2-aryl-1H-indol-3-yl)ethynes via 5-exo-Digonal Double Cyclization Reactions of 1,4-Bis(2-isocyanophenyl)buta-1,3-diyne\nwith Aryl Grignard Reagents","volume":"82","author":"Ishikawa","year":"2017","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit12p","doi-asserted-by":"publisher","first-page":"133","DOI":"10.1246\/cl.180888","article-title":"Synthesis\nand Properties of a Conjugated Macrocyclic Molecule Incorporating\nTwo Quinoline Moieties","volume":"48","author":"Shimasaki","year":"2019","journal-title":"Chem. Lett."},{"key":"2026100909091000000_cit12q","doi-asserted-by":"publisher","first-page":"3220","DOI":"10.1002\/adsc.202100339","article-title":"Palladium-Catalyzed Domino Synthesis of 2,3-Difunctionalized\nIndoles via Migratory Insertion of Isocyanides in\nBatch and Continuous Flow","volume":"363","author":"Chen","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"2026100909091000000_cit12r","doi-asserted-by":"publisher","first-page":"284","DOI":"10.1021\/acs.orglett.1c03916","article-title":"2,3-Difunctionalized Indoles via Radical Acylation or Trifluoromethylation of ortho-Alkynylphenyl Isonitriles","volume":"24","author":"Leifert","year":"2022","journal-title":"Org.\nLett."},{"key":"2026100909091000000_cit12s","doi-asserted-by":"publisher","first-page":"8379","DOI":"10.1021\/acs.joc.3c00405","article-title":"Bicyclic Amidine-Triggered Cyclization\nof o-Alkynylisocyanobenzenes: Synthesis of Lactam-Derived\nQuinolines","volume":"88","author":"Xiong","year":"2023","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit12t","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202201269","article-title":"Photoinduced Synthesis of Bisphosphinated\nQuinoxalines via Radical Cyclization of o-Diisocyanoarenes with Diphosphines","volume":"18","author":"Yamamoto","year":"2023","journal-title":"Chem.\n- Asian J."},{"key":"2026100909091000000_cit12u","doi-asserted-by":"publisher","first-page":"5067","DOI":"10.1039\/D4QO00683F","article-title":"A Visible-Light-Induced Cascade Cyclization\nStrategy for the Synthesis of N,S-Containing Polycyclic\nCompounds","volume":"11","author":"Yang","year":"2024","journal-title":"Org. Chem. Front."},{"key":"2026100909091000000_cit12v","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202500429","article-title":"Enlarged-Triquinoline (Enl-TQ): Disparity in Chemical\nBehaviors by Geometric Scaling of the Trimeric Quinoline Ring System","volume":"20","author":"Yamashita","year":"2025","journal-title":"Chem. - Asian J."},{"key":"2026100909091000000_cit12w","doi-asserted-by":"publisher","first-page":"4449","DOI":"10.1021\/acs.joc.6c00135","article-title":"Silver\/Indium-Catalyzed Cyclization\nof o-Alkynylisocyanobenzenes with Nitriles for the\nSynthesis of Amide-Substituted Quinolines","volume":"91","author":"Liu","year":"2026","journal-title":"J.\nOrg. Chem."},{"key":"2026100909091000000_cit12x","doi-asserted-by":"publisher","first-page":"7050","DOI":"10.1039\/C8OB01882K","article-title":"Synthesis of 3-Substituted Quinolin-2(1H)-ones via the Cyclization of o-Alkynylisocyanobenzenes","volume":"16","author":"Charoenpol","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"2026100909091000000_cit12y","doi-asserted-by":"publisher","first-page":"8553","DOI":"10.1039\/C8OB02338G","article-title":"Sulfinates and Thiocyanates Triggered 6-endo Cyclization of o-Alkynylisocyanobenzenes","volume":"16","author":"Khaikate","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"2026100909091000000_cit12z","doi-asserted-by":"publisher","first-page":"7050","DOI":"10.1002\/ejoc.201901209","article-title":"Azide-Triggered Bicyclization of o-Alkynylisocyanobenzenes:\nSynthesis of Tetrazolo [1, 5-a] quinolines","volume":"2019","author":"Khaikate","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"2026100909091000000_cit12aa","doi-asserted-by":"publisher","first-page":"6338","DOI":"10.1021\/acs.joc.0c00003","article-title":"Alkanethiol-Mediated Cyclization\nof o-Alkynylisocyanobenzenes: Synthesis of Bis-Thiolated Indole Derivatives","volume":"85","author":"La-Ongthong","year":"2020","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit12ab","doi-asserted-by":"publisher","first-page":"1411","DOI":"10.1055\/a-1784-2513","article-title":"Cyclization of o-Alkynylisocyanobenzenes\nwith 1,3-Dicarbonyl Compounds","volume":"33","author":"La-ongthong","year":"2022","journal-title":"Synlett"},{"key":"2026100909091000000_cit12ac","doi-asserted-by":"publisher","first-page":"13273","DOI":"10.1039\/D6NJ01905F","article-title":"Recent Advances in Cascade Cyclization\nof ortho-Alkynyl and Alkenyl Isocyanides to Access Heterocyclic Scaffolds","volume":"50","author":"Venkat Shivaji Ramarao","year":"2026","journal-title":"New J. Chem."},{"key":"2026100909091000000_cit13a","doi-asserted-by":"publisher","first-page":"15131","DOI":"10.1021\/acs.joc.9b02081","article-title":"Synthesis of Indolo- and Benzothieno[2,3-b]quinolines by a Cascade Cyclization of o-Alkynylisocyanobenzene\nDerivatives","volume":"84","author":"Khaikate","year":"2019","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit13b","doi-asserted-by":"publisher","first-page":"16333","DOI":"10.1039\/D2NJ02791G","article-title":"Synthesis of Indolo-\nand Benzothieno[3,2-c]quinolines via POCl3 Mediated Tandem Cyclization of o-Alkynylisocyanobenzenes Derived from o-Alkynyl-N-phenylformamides","volume":"46","author":"Uppalabat","year":"2022","journal-title":"New J. Chem."},{"key":"2026100909091000000_cit14","doi-asserted-by":"publisher","first-page":"7844","DOI":"10.1021\/jo9016309","article-title":"PdCl2-Promoted Electrophilic Annulation of 2-Alkynylphenol Derivatives\nwith Disulfides or Diselenides in the Presence of Iodine","volume":"74","author":"Du","year":"2009","journal-title":"J. Org. Chem."},{"key":"2026100909091000000_cit15a","doi-asserted-by":"publisher","first-page":"3437","DOI":"10.1002\/adsc.201700509","article-title":"Synthesis of 1,2-Dihydrocyclobuta[b]quinoline Derivatives\nfrom Isocyanophenyl-Substituted Methylenecyclopropanes","volume":"359","author":"Liu","year":"2017","journal-title":"Adv. Synth. Catal."},{"key":"2026100909091000000_cit15b","doi-asserted-by":"publisher","first-page":"676","DOI":"10.1021\/acs.orglett.2c04314","article-title":"Copper-Catalyzed Cyclization\nof 2-Alkynylanilines to Give 2-Haloalkoxy-3-alkyl(aryl)quinolines","volume":"25","author":"Lu","year":"2023","journal-title":"Org. Lett."},{"key":"2026100909091000000_cit15c","doi-asserted-by":"publisher","first-page":"5599","DOI":"10.1021\/acs.orglett.1c01484","article-title":"Solvent-Dependent\nCyclization of 2-Alkynylanilines and ClCF2COONa for the\nDivergent Assembly of N-(Quinolin-2-yl)amides and\nQuinolin-2(1H)-ones","volume":"23","author":"Wang","year":"2021","journal-title":"Org. Lett."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01498","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/40\/13426\/68624820\/acs.joc.6c01498.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/40\/13426\/68624820\/acs.joc.6c01498.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T13:25:28Z","timestamp":1791552328000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/40\/13426\/5436854\/Ag-I-Promoted-Cascade-Cyclization-of-1-Isocyano-2"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,23]]},"references-count":91,"journal-issue":{"issue":"40","published-online":{"date-parts":[[2026,9,23]]},"published-print":{"date-parts":[[2026,10,9]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01498","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,23]]}}}