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, 2021 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume:
  • Publication Date: 2021
  • Doi Number: 10.1002/ejoc.202100483
  • Title of Journal : EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

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.