EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol.2021, no.29, pp.4107-4124, 2021 (SCI-Expanded)
Article / Article
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Chimica
1,3-Dithiane, A3-coupling, Iodocyclization, Iodothiophene, Sulfonium ion
Istanbul Technical University Affiliated:
1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30-87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30-94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A(3)-coupling reaction.