{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T07:18:55Z","timestamp":1787642335983,"version":"build-2736575974"},"reference-count":0,"publisher":"Swiss Chemical Society","issue":"7-8","license":[{"start":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T00:00:00Z","timestamp":1787097600000},"content-version":"unspecified","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chimia"],"abstract":"<jats:p>Isothiazoles are valuable heterocycles in agrochemical and pharmaceutical research, yet they remain synthetically less accessible than their isoxazole counterparts. We report here a gold-catalyzed cyclization of propargylic N-tert-butanesulfinamides that provides direct and efficient access to isothiazoles under mild conditions. The transformation proceeds through an unusual cascade: cationic gold activation of the alkyne triggers a 5-endo-dig ring closure with sulfur as the nucleophile followed by irreversible loss of the tert-butyl group and dehydrative aromatization. The substrate scope encompasses a range of alkyl and aryl substituents, affording isothiazoles in yields of up to 79%. Reaction monitoring and isolation of key intermediates establish that the cyclic sulfinamide is a direct precursor to the aromatic product and that protic solvents, particularly acetic acid, facilitate the cascade of events, dramatically reducing reaction times. A complementary base-catalyzed pathway from CF3-substituted substrates selectively delivers cyclic sulfoximines, demonstrating that both heterocyclic classes are accessible from a common precursor by simply switching the activation mode. These results originate from a serendipitous observation made during insecticide research at Syngenta and have broader implications for the design of sulfur-containing heterocyclic scaffolds<\/jats:p>","DOI":"10.2533\/chimia.2026.473","type":"journal-article","created":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T22:35:13Z","timestamp":1787092513000},"page":"473-478","source":"Crossref","is-referenced-by-count":0,"title":["Unified Gold-Catalyzed Cyclization Approach Towards Isothiazoles from Propargylic Sulfinamides"],"prefix":"10.2533","volume":"80","author":[{"given":"Nada","family":"Sa\u00efdi","sequence":"first","affiliation":[{"name":"Syngenta Crop Protection, Schaffhauserstrasse, CH-4332 Stein, Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas","family":"Simonet","sequence":"additional","affiliation":[{"name":"Syngenta Crop Protection, Schaffhauserstrasse, CH-4332 Stein, Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel P.","family":"Kloer","sequence":"additional","affiliation":[{"name":"Syngenta Crop Protection, Schaffhauserstrasse, CH-4332 Stein, Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mark","family":"Montgomery","sequence":"additional","affiliation":[{"name":"Syngenta Crop Protection, Schaffhauserstrasse, CH-4332 Stein, Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Myriem","family":"El Qacemi","sequence":"additional","affiliation":[{"name":"Syngenta Crop Protection, Schaffhauserstrasse, CH-4332 Stein, Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1442","published-online":{"date-parts":[[2026,8,19]]},"container-title":["CHIMIA"],"original-title":[],"link":[{"URL":"https:\/\/www.chimia.ch\/chimia\/article\/download\/2026_473\/2026_473","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.chimia.ch\/chimia\/article\/download\/2026_473\/2026_473","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T06:22:26Z","timestamp":1787638946000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.chimia.ch\/chimia\/article\/view\/2026_473"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,19]]},"references-count":0,"journal-issue":{"issue":"7-8","published-online":{"date-parts":[[2026,8,19]]}},"URL":"https:\/\/doi.org\/10.2533\/chimia.2026.473","relation":{},"ISSN":["2673-2424","0009-4293"],"issn-type":[{"value":"2673-2424","type":"electronic"},{"value":"0009-4293","type":"print"}],"subject":[],"published":{"date-parts":[[2026,8,19]]}}}