{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T02:02:59Z","timestamp":1760148179039,"version":"build-2065373602"},"reference-count":36,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2023,4,5]],"date-time":"2023-04-05T00:00:00Z","timestamp":1680652800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Oklahoma State University Foundation","award":["BIR-9512269","CHE-1726630"],"award-info":[{"award-number":["BIR-9512269","CHE-1726630"]}]},{"name":"College of Arts and Sciences at Oklahoma State University","award":["BIR-9512269","CHE-1726630"],"award-info":[{"award-number":["BIR-9512269","CHE-1726630"]}]},{"DOI":"10.13039\/100000001","name":"NSF","doi-asserted-by":"publisher","award":["BIR-9512269","CHE-1726630"],"award-info":[{"award-number":["BIR-9512269","CHE-1726630"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Oklahoma State Regents for Higher Education","award":["BIR-9512269","CHE-1726630"],"award-info":[{"award-number":["BIR-9512269","CHE-1726630"]}]},{"name":"W.M. Keck Foundation","award":["BIR-9512269","CHE-1726630"],"award-info":[{"award-number":["BIR-9512269","CHE-1726630"]}]},{"name":"Conoco, Inc.","award":["BIR-9512269","CHE-1726630"],"award-info":[{"award-number":["BIR-9512269","CHE-1726630"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of new Morita\u2013Baylis\u2013Hillman acetates were prepared and reacted with methanesulfonamide (K2CO3, DMF, 23 \u00b0C) to produce tertiary dihydroquinoline sulfonamides in high yields. Subsequent efforts to eliminate the methylsulfonyl group from these derivatives (K2CO3, DMF, 90 \u00b0C) as a route to quinolines were met with mixed results. Although dihydroquinoline sulfonamides prepared from ethyl acrylate and acrylonitrile generally underwent elimination to give excellent yields of quinolines, those generated from 3-buten-2-one failed to undergo elimination and instead decomposed. The failure of these ketone substrates to aromatize presumably derives from the enolizable methyl ketone at C-3. Finally, the attempted aromatization of the acrylate-derived 6,7-difluoro-1,2-dihydroquinoline sulfonamide demonstrated that other interesting processes could occur in preference to the desired elimination.<\/jats:p>","DOI":"10.3390\/molecules28073256","type":"journal-article","created":{"date-parts":[[2023,4,6]],"date-time":"2023-04-06T01:10:27Z","timestamp":1680743427000},"page":"3256","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis and Elimination Pathways of 1-Methanesulfonyl-1,2-dihydroquinoline Sulfonamides"],"prefix":"10.3390","volume":"28","author":[{"given":"Ebenezer","family":"Ametsetor","sequence":"first","affiliation":[{"name":"Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kwabena","family":"Fobi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-7927-5655","authenticated-orcid":false,"given":"Richard A.","family":"Bunce","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,4,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Annor-Gyamfi, J.K., Ametsetor, E., Meraz, K., and Bunce, R.A. (2021). Dihydroquinolines, dihydronaphthyridines and quinolones by domino reactions of Morita-Baylis-Hillman acetates. Molecules, 26.","DOI":"10.3390\/molecules26040890"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Annor-Gyamfi, J.K., Ametsetor, E., Meraz, K., and Bunce, R.A. (2020). Naphthalenes and Quinolines by Domino Reactions of Morita\u2013Baylis\u2013Hillman Acetates. Molecules, 25.","DOI":"10.3390\/molecules25215168"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"467","DOI":"10.1007\/BF03247234","article-title":"Microwave-assisted Michael addition of sulfonamides to \u03b1,\u03b2-unsaturated esters: A rapid entry to protected \u03b2-amino acid synthesis","volume":"4","author":"Imanzadeh","year":"2007","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1007\/BF03246142","article-title":"An efficient solventless method for the synthesis of N,N-dialkyl sulfonamide derivatives","volume":"5","author":"Zare","year":"2008","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"480","DOI":"10.1002\/ajoc.201300062","article-title":"Synthesis of highly functionalized aminoindolizines by titanium(IV) chloride mediated cycloisomerization and phosphine-catalyzed aza-Michael addition reactions","volume":"2","author":"Wang","year":"2013","journal-title":"Asian J. Org. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"532","DOI":"10.1002\/jhet.1750","article-title":"Tandem aza-Michael-aldol reactions: One-pot synthesis of functionalized piperidine derivatives","volume":"51","author":"Huang","year":"2013","journal-title":"J. Heterocycl. Chem."},{"key":"ref_7","first-page":"1346","article-title":"The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solvent-free conditions","volume":"54","author":"Douraki","year":"2015","journal-title":"Indian J. Chem. Sect. B Org. Chem. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1702","DOI":"10.1002\/ejoc.201501618","article-title":"Enantioselective catalytic domino aza-Michael-Henry reactions: One-pot asymmetric synthesis of 3-nitro-1,2-dihydroquinolines via iminium activation","volume":"2016","author":"Luo","year":"2016","journal-title":"Eur. J. Org. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1793","DOI":"10.1016\/j.cclet.2017.04.017","article-title":"Asymmetric catalyzed intramolecular aza-Michael reaction mediated by quinine-derived primary amines","volume":"28","author":"Zhai","year":"2017","journal-title":"Chin. Chem. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"9397","DOI":"10.1002\/anie.201805020","article-title":"Chinchonamine squaramide catalyzed asymmetric aza-Michael reaction: Dihydroisoquinolines and tetrahydropyridines","volume":"57","author":"Roy","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"482","DOI":"10.1080\/00304940409356635","article-title":"N-(Nitrophenyl) benzamide and benzenesulfonamide derivatives by nucleophilic aromatic substitution","volume":"36","author":"Bunce","year":"2004","journal-title":"Org. Prep. Proced. Int."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2507","DOI":"10.1021\/jo00876a042","article-title":"Nitrogen acids. 1. Carboxamides and sulfonamides","volume":"41","author":"Bordwell","year":"1976","journal-title":"J. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3330","DOI":"10.1021\/jo00297a063","article-title":"Acidities of carboxamides, hydroxamic acids, carbohydrazides, benzenesulfonamides, and benzenesulfonohydrazides in DMSO solution","volume":"55","author":"Bordwell","year":"1990","journal-title":"J. Org. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1471","DOI":"10.1126\/science.1962206","article-title":"The atom economy\u2013A search for synthetic efficiency","volume":"254","author":"Trost","year":"1991","journal-title":"Science"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1002\/anie.199502591","article-title":"Atom economy\u2014A challenge for organic synthesis: Homogeneous catalysis leads the way","volume":"90","author":"Trost","year":"1995","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_16","unstructured":"Trost, B.M. (2012). Handbook of Green Chemistry, Wiley Online Library."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3737","DOI":"10.1016\/S0040-4039(01)00552-4","article-title":"Synthesis of 3-quinolinecarboxylic acid esters from the Baylis\u2013Hillman adducts of 2-halobenzaldehyde N-tosylimines","volume":"42","author":"Kim","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1185","DOI":"10.1002\/adsc.201201033","article-title":"Copper-catalyzed domino SN2\/Coupling reaction: A versatile and facile synthesis of cyclic compounds from Baylis-Hillman acetates","volume":"355","author":"Niu","year":"2013","journal-title":"Adv. Synth. Catal."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5505","DOI":"10.1039\/C5OB02063H","article-title":"Structure-based design of 3-carboxy-substituted 1,2,3,4-tetrahydroquinolines as inhibitors of myeloid cell leukemia-1 (Mcl-1)","volume":"14","author":"Chen","year":"2015","journal-title":"Org. Biomol. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4441","DOI":"10.1016\/j.bmc.2018.07.042","article-title":"Novel tertiary sulfonamides as potent anti-cancer agents","volume":"26","author":"Okolotowicz","year":"2018","journal-title":"Bioorganic Med. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/j.ejmech.2018.05.034","article-title":"Synthesis, characterization and biological evaluation of tertiary sulfonamide derivatives of pyridyl-indole based heteroaryl chalcone as potential carbonic anhydrase IX inhibitors and anticancer agents","volume":"155","author":"Peerzada","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_22","first-page":"2869","article-title":"Evaluation of novel coumarin-proline sulfonamide hybrids as anticancer and antidiabetic agents","volume":"49","author":"Durgapal","year":"2019","journal-title":"Synth. Commun."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1080\/14756366.2016.1238367","article-title":"Synthesis and bioactivity of several new hetaryl sulfonamides","volume":"32","author":"Taslimi","year":"2017","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"11209","DOI":"10.1021\/acs.jmedchem.8b01344","article-title":"Design and optimization of sulfone pyrrolidine sulfonamide antagonists of transient receptor potential vanilloid-4 with in vivo activity in a pulmonary edema model","volume":"61","author":"Pero","year":"2018","journal-title":"J. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1080\/00397911.2020.1870238","article-title":"Sulfonamide synthesis under green conditions","volume":"51","author":"Mondal","year":"2021","journal-title":"Synth. Commun."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2342","DOI":"10.1021\/jo980011z","article-title":"An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethanesulfonate","volume":"63","author":"Procopiou","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3190","DOI":"10.1016\/j.tetlet.2016.06.033","article-title":"Nucleophilic additions to polarized vinylarenes","volume":"57","author":"Gnanasekaran","year":"2016","journal-title":"Tetrahedron Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1849","DOI":"10.1080\/00397911.2016.1234622","article-title":"Synthesis of ciprofloxacin-based compounds: A review","volume":"46","author":"Akhtar","year":"2016","journal-title":"Synth. Commun."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2549","DOI":"10.1039\/C9OB02587A","article-title":"Synthetic and mechanistic aspects of sulfonyl migrations","volume":"18","author":"Flynn","year":"2020","journal-title":"Org. Biomol. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1693","DOI":"10.1002\/anie.201108144","article-title":"Highly regioselective migration of the sulfonyl group: Easy access to functionalized pyrroles","volume":"51","author":"Xin","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1463","DOI":"10.1039\/c3ob27493d","article-title":"Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process","volume":"11","author":"Tummatorn","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_32","unstructured":"Bruker (APEX3, 2018). APEX3, version 2018.7-2."},{"key":"ref_33","unstructured":"Bruker (SAINT, 2016). SAINT, version 8.38A."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","article-title":"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"ref_35","first-page":"3","article-title":"SHELXT-Integrated Space-Group and Crystal-Structure Determination","volume":"A71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."},{"key":"ref_36","first-page":"3","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/7\/3256\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:10:42Z","timestamp":1760123442000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/7\/3256"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,4,5]]},"references-count":36,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2023,4]]}},"alternative-id":["molecules28073256"],"URL":"https:\/\/doi.org\/10.3390\/molecules28073256","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2023,4,5]]}}}