Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines

Ismailoglu E., Mert Z., Dinc M., Kaya K., Yücel B.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol.2021, no.29, pp.4107-4124, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 2021 Issue: 29
  • Publication Date: 2021
  • Doi Number: 10.1002/ejoc.202100483
  • Journal Name: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Chimica
  • Page Numbers: pp.4107-4124
  • Keywords: 1,3-Dithiane, A3-coupling, Iodocyclization, Iodothiophene, Sulfonium ion
  • Istanbul Technical University Affiliated: Yes

Abstract

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.