Cyclization of cysteinylglycine sulfoxides under Pummerer reaction conditions

S Wolfe, PM Kazmaier, H Auksi

Index: Wolfe,S. et al. Canadian Journal of Chemistry, 1979 , vol. 57, # 18 p. 2412 - 2425

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Citation Number: 14

Abstract

A number of sulfoxides derived from 3-benzylthiopropionic acid, S-benzylcysteine, and S- phenylcystelne have been synthesized and exposed to typical Pummerer reaction conditions. Cyclization of the S-benzyl sulfoxides to six-membered or seven-membered heterocyclic rings (1, 3-thiazin-4-ones and 1, 3, 6-oxathiazepines) is observed only in acetic anhydride solvent and only after conversion of the carboxyl group to an amide or peptide. ...