Electrophilic α-thiocyanation of chiral and achiral N-acyl imides. A convenient route to 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones

J R Falck, Shuanhu Gao, Ravi Naga Prasad, Sreenivasulu Reddy Koduru

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

Electrophilic α-thiocyanation of N-acyl carboximides using N-thiocyanatosuccinimide and hydrolytic cyclization of the adducts affords 5-substituted and 5,5-disubstituted 2,4-thiazolidinediones in good overall yields. α-Thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.

Original languageEnglish (US)
Pages (from-to)1768-1771
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume18
Issue number6
DOIs
StatePublished - Mar 15 2008

Keywords

  • Asymmetric
  • Enolate
  • Heterocycle
  • Thiazolidinedione
  • Thiocyanate

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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