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Paper | Regular issue | Vol 63, No. 10, 2004, pp.2243-2267
Published online, 7th September, 2004
DOI: 10.3987/COM-04-10137
Synthesis, Oxidation and Dehydrogenation of Cyclic N,O- and N,S-Acetals. Part 1. Transformation of N,S-Acetals: 3-Acyl-1,3,4-thiadiazolines

László Somogyi

*Department of Organic Chemistry, University of Debrecen, P.O.Box 20, H-4010 Debrecen, Hungary

Abstract

Aldehyde and ketone thiosemicarbazones are synthesized and cyclized into 3-acyl-1,3,4-thiadiazolines under acylating conditions. Reactions of the 2-monosubstituted heterocycles with oxidizing and dehydrogenating agents (KMnO4 or for the first time with CAN, DDQ, IBDA) lead to the formation of thiadiazoles. CAN oxidation of 2,2-disubstituted 3-acyl-1,3,4-thiadiazolines regenerates the parent ketones efficiently.