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The reaction begins with conjugate addition of the thiolate to the 2-aminocinnamic acid derivatives, generating \u03b2-sulfide-substituted dihydrocinnamic acid intermediates. These intermediates can adopt conformations that bring the amino and carboxyl groups into close proximity through free rotation about the C\u03b1\u2013C\u03b2 single bond. Subsequent intramolecular condensation between the amino and carboxyl groups, followed by elimination of hydrogen sulfide, furnishes the desired 2-quinolones. A broad range of 2-aminocinnamic acid derivatives are compatible with this transformation, delivering the corresponding 2-quinolone derivatives in excellent yields. Furthermore, this method is also applicable to the synthesis of all regioisomers of 2-aza-quinolones from 2-amino-aza-cinnamate derivatives. The simple operation, facile isolation of quinolones by recrystallization, and gram-scale scalability further highlight the practical utility of this protocol.<\/jats:p>","DOI":"10.1021\/acsomega.5c13222","type":"journal-article","created":{"date-parts":[[2026,2,23]],"date-time":"2026-02-23T12:29:27Z","timestamp":1771849767000},"page":"15442-15451","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis of 2\u2011Quinolones\nvia Thiolate-Mediated\nCyclization of (\n                    <i>E<\/i>\n                    )\u20112-Aminocinnamic Acid Derivatives"],"prefix":"10.1021","volume":"11","author":[{"given":"Tae Won","family":"Kim","sequence":"first","affiliation":[{"name":"Korea University , , 145 Anam-ro, Seongbuk-gu , ,","place":["Seoul, Republic of Korea, 02841"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nuo Ming","family":"Goh","sequence":"additional","affiliation":[{"name":"Korea University , , 145 Anam-ro, Seongbuk-gu , ,","place":["Seoul, Republic of Korea, 02841"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheol-Hong","family":"Cheon","sequence":"additional","affiliation":[{"name":"Korea University , , 145 Anam-ro, Seongbuk-gu , ,","place":["Seoul, Republic of Korea, 02841"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,2,23]]},"reference":[{"key":"2026081508100412900_cit1a","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202401936","article-title":"Recent Updates on\nAntibacterial Quinolones: Green Synthesis, Mode of Interaction and\nStructure\u2013Activity Relationship","volume":"22","author":"Sharma","year":"2025","journal-title":"Chem.\nBiodivers."},{"key":"2026081508100412900_cit1b","doi-asserted-by":"publisher","first-page":"5129","DOI":"10.1007\/s11030-024-11092-4","article-title":"Quinoline\nand Quinolone Carboxamides: A Review of Anticancer Activity with Detailed\nStructure\u2013Activity Relationship Analysis","volume":"29","author":"Thomas","year":"2025","journal-title":"Mol. 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