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

ABSTRACT: Electrophilic alpha-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. Alpha-thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization.

SUBMITTER: Falck JR

PROVIDER: S-EPMC2329916 | biostudies-literature | 2008 Mar

REPOSITORIES: biostudies-literature

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

Falck J R JR Gao Shuanhu S Prasad Ravi Naga RN Koduru Sreenivasulu Reddy SR

Bioorganic & medicinal chemistry letters 20080216 6

Electrophilic alpha-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. Alpha-thiocyanation of chiral N-acyl carboximides proceeds with excellent diastereoselectivity, although partial racemization occurs during subsequent cyclization. ...[more]

PMID: 18308568

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