Base-Mediated Rearrangement of α-Dithioacetyl Propargylamines via Expansion of Dithioacetyl Ring: Synthesis of Medium-Sized S,S-Heterocycles

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

Organic Letters, vol.25, no.22, pp.4028-4032, 2023 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 25 Issue: 22
  • Publication Date: 2023
  • Doi Number: 10.1021/acs.orglett.3c01118
  • Journal Name: Organic Letters
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, EMBASE, MEDLINE
  • Page Numbers: pp.4028-4032
  • Istanbul Technical University Affiliated: Yes

Abstract

Base-mediated rearrangement of 1,3-dithianyl-substituted propargylamines in DMF via expansion of the dithiane ring has been reported. The rearrangement provided 9-membered amino-functionalized sulfur-containing heterocycles (dithionine derivatives) in good yields under mild conditions. Propargylamines bearing 5-membered 1,3-dithiolane and 7-membered 1,3-dithiepane rings rearranged in a similar manner yielding 8- and 10-membered S,S-heterocycles, respectively.