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Communication | Regular issue | Vol 24, No. 5, 1986, pp.1193-1196
Published online, 1st January, 1970
DOI: 10.3987/R-1986-05-1193
1,2,5-Thiadiazole-1-oxides. V. Ring Transformations to Pyrazine, 1,2,4-Thiadiazole and Pyrrole

Sandor Karady,* Joseph S. Amato, Robert A. Reamer, and Lonard M. Weinstock

*Division of Merck & Co., Inc., Merck Research Laboratories, P.O.Box 2000, Rahway, NJ 07065, U.S.A.

Abstract

Rearrangement of 2-alkyl-1,2,5-thiadiazole-3-on-1-oxides to pyrazine, 1,2,4-thiadiazole and pyrrole derivatives is described. Ring opening to a sufinylamine and cyclization by cycloaddition or nucleophilic addition is the postulated mechanism.