Iodocyclization of S–(homo)propargyl dithiocarbamates: Regiospecific synthesis of 2-imino(iminium)-1, 3-dithiolanes/dithianes/dithiepanes

Farinaz Soleymani, Azim Ziyaei Halimehjani, Farzane Jafari Asar, Gregory R.J. Thatcher

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12 Scopus citations

Abstract

An efficient, simple and regiospecific protocol for the synthesis of iodine-containing 2-imino(iminium)1,3- dithiolanes/dithianes/dithiepanes is reported via iodocyclization of corresponding S-(homo)propargyl dihtiocarbamates with molecular iodine. The reactions are regiospecific and only the exo-dig cyclization products were observed in all the cases. In addition, mild reaction conditions, high yields, easy purification, and using inexpensive reagents are the main advantages of this protocol.

Original languageEnglish (US)
Article number154702
JournalTetrahedron Letters
Volume128
DOIs
StatePublished - Sep 19 2023

Keywords

  • 1,3-dithiolanes
  • Alkynes
  • Dithiocarbamates
  • Exo-dig cyclization
  • Iodocyclization

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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