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Paper | Regular issue | Vol 68, No. 4, 2006, pp.679-686
Published online, 3rd March, 2006
DOI: 10.3987/COM-05-10662
Synthesis of Chiral Thiazolo[3,4-a]pyrazine-5,8-diones

Teresa M. V. D. Pinho e Melo,* Susana M. M. Lopes, António M. d’A. Rocha Gonsalves, José A. Paixão, Ana Matos Beja, and Manuela Ramos Silva

*Department of Chemistry, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal

Abstract

A synthetic approach to chiral (3R,8aR)-3-phenyltetrahydro- thiazolo[3,4-a]pyrazine-5,8-diones starting from a (2S,4R)- and (2R,4R)-diastereoisomeric mixture of 2-phenylthiazolidine is described. The diastereoselective N-acylation of the thiazolidine followed by condensation with amines affords the chiral 1,3-thiazolidine-annulated system. The structure of (3R,8aR)-7-(methoxycarbonylmethyl)-3-phenyltetrahydrothiazolo[3,4-a]pyrazine-5,8-dione was determined by X-Ray crystallography.