{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T02:07:31Z","timestamp":1791511651448,"version":"4.3.4"},"reference-count":30,"publisher":"American Chemical Society (ACS)","issue":"10","license":[{"start":{"date-parts":[[2020,9,28]],"date-time":"2020-09-28T00:00:00Z","timestamp":1601251200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccby_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100004319","name":"Pfizer","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100004319","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100004325","name":"AstraZeneca","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100004325","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009945","name":"Merck KGaA","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100009945","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004189","name":"Max-Planck-Gesellschaft","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100004189","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,10,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Multicomponent Petasis reaction has been widely applied for the synthesis of functionalized amine building blocks and biologically active compounds. Employing primary aromatic amines that are not typical reactive substrates contributes to expand the application scope of the Petasis reaction. In this study, we demonstrated the synthesis of functionalized 2-aminothiophenes using Gewald-reaction-derived 2-aminothiophenes as the amine substrates, whose low reactivity in the Petasis reaction was overcome using hexafluoro-2-propanol as the solvent in a mild condition. The obtained Petasis products are amenable for further transformations owing to the presence of multiple functional handles. A following intramolecular cyclization of selected Petasis products afforded substituted tricyclic heterocycles that incorporate a pharmaceutically interesting thienodiazepine moiety.<\/jats:p>","DOI":"10.1021\/acscombsci.0c00173","type":"journal-article","created":{"date-parts":[[2020,9,28]],"date-time":"2020-09-28T11:05:08Z","timestamp":1601291108000},"page":"495-499","source":"Crossref","is-referenced-by-count":17,"title":["Multicomponent Petasis Reaction for the Synthesis\nof Functionalized 2-Aminothiophenes and Thienodiazepines"],"prefix":"10.1021","volume":"22","author":[{"given":"Jimin","family":"Hwang","sequence":"first","affiliation":[{"name":"Max Planck Institute of Molecular Physiology , , ,","place":["Dortmund, Germany, 44227"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lydia","family":"Borgelt","sequence":"additional","affiliation":[{"name":"Max Planck Institute of Molecular Physiology , , ,","place":["Dortmund, Germany, 44227"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0186-1086","authenticated-orcid":true,"given":"Peng","family":"Wu","sequence":"additional","affiliation":[{"name":"Max Planck Institute of Molecular Physiology , , ,","place":["Dortmund, Germany, 44227"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,9,28]]},"reference":[{"issue":"4","key":"2026090316440873800_cit1","doi-asserted-by":"publisher","first-page":"583","DOI":"10.1016\/S0040-4039(00)61625-8","article-title":"The boronic\nacid Mannich reaction - A new method for the synthesis of geometrically\npure allylamines","volume":"34","author":"Petasis","year":"1993","journal-title":"Tetrahedron Lett."},{"issue":"10","key":"2026090316440873800_cit2","doi-asserted-by":"publisher","first-page":"6169","DOI":"10.1021\/cr100108k","article-title":"Boronic acids and esters in the Petasis-borono Mannich\nmulticomponent reaction","volume":"110","author":"Candeias","year":"2010","journal-title":"Chem. 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Chem."},{"issue":"9","key":"2026090316440873800_cit6","doi-asserted-by":"publisher","first-page":"2700","DOI":"10.1002\/anie.201812620","article-title":"Introducing the Petasis reaction for late-stage multicomponent\ndiversification, labeling, and stapling of peptides","volume":"58","author":"Ricardo","year":"2019","journal-title":"Angew. Chem., Int. Ed."},{"issue":"1","key":"2026090316440873800_cit7","doi-asserted-by":"publisher","first-page":"53","DOI":"10.1039\/C9SC04697F","article-title":"Secondary amine selective\nPetasis (SASP) bioconjugation","volume":"11","author":"Sim","year":"2020","journal-title":"Chem. Sci."},{"issue":"9","key":"2026090316440873800_cit8","doi-asserted-by":"publisher","first-page":"115441","DOI":"10.1016\/j.bmc.2020.115441","article-title":"Translation\nof the copper\/bipyridine-promoted Petasis reaction to solid phase-coupled\nDNA for encoded library synthesis","volume":"28","author":"Potowski","year":"2020","journal-title":"Bioorg. Med.\nChem."},{"issue":"23","key":"2026090316440873800_cit9","doi-asserted-by":"publisher","first-page":"9353","DOI":"10.1021\/acs.orglett.9b03553","article-title":"High-throughput solid-phase building\nblock synthesis for DNA-encoded libraries","volume":"21","author":"Zambaldo","year":"2019","journal-title":"Org.\nLett."},{"issue":"12","key":"2026090316440873800_cit10","doi-asserted-by":"publisher","first-page":"4853","DOI":"10.1021\/acs.orglett.9b01747","article-title":"Photoredox-catalyzed\nmulticomponent Petasis reaction with alkyltrifluoroborates","volume":"21","author":"Yi","year":"2019","journal-title":"Org. Lett."},{"key":"2026090316440873800_cit11","doi-asserted-by":"publisher","first-page":"465","DOI":"10.1016\/j.ejmech.2017.09.039","article-title":"2-Aminothiophene scaffolds: Diverse biological and\npharmacological attributes in medicinal chemistry","volume":"140","author":"Bozorov","year":"2017","journal-title":"Eur. J. Med. 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Commun."},{"key":"2026090316440873800_cit29","doi-asserted-by":"publisher","first-page":"27","DOI":"10.1016\/j.ddtec.2018.06.010","article-title":"Petasis three-component\nreactions for the synthesis of diverse heterocyclic scaffolds","volume":"29","author":"Wu","year":"2018","journal-title":"Drug Discovery Today: Technol."},{"issue":"19","key":"2026090316440873800_cit30","doi-asserted-by":"publisher","first-page":"2925","DOI":"10.1055\/s-2007-983902","article-title":"Fluorinated\nalcohols as solvents, cosolvents and additives in homogeneous catalysis","volume":"2007","author":"Shuklov","year":"2007","journal-title":"Synthesis"}],"container-title":["ACS Combinatorial Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acscombsci.0c00173","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsccc\/article-pdf\/22\/10\/495\/67385889\/acscombsci.0c00173.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsccc\/article-pdf\/22\/10\/495\/67385889\/acscombsci.0c00173.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T20:44:16Z","timestamp":1788468256000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsccc\/article\/22\/10\/495\/605876\/Multicomponent-Petasis-Reaction-for-the-Synthesis"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,9,28]]},"references-count":30,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2020,9,28]]},"published-print":{"date-parts":[[2020,10,12]]}},"URL":"https:\/\/doi.org\/10.1021\/acscombsci.0c00173","relation":{},"ISSN":["2156-8952","2156-8944"],"issn-type":[{"value":"2156-8952","type":"print"},{"value":"2156-8944","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,9,28]]}}}