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Report | Regular issue | Vol 16, No. 9, 1981, pp.1565-1568
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1565
1,2,5-Thiadiazole-1-oxides. II. The Chemistry of the Amines

Sandor Karady,* Joseph S. Amato, Daniel Dortmund, Robert A. Raemer, and Leonard M. Weinstock

*Division of Merec and Co., Inc, Merck Sharp and Dohme Research Laboratories, Rahway, New Jersey 07065, U.S.A.

Abstract

Amino-substituted 1,2,5-thiadiazole-1-oxides form salts with NaOMe or NaH. These reacted with alkyl halides, acyl chlorides, isocyanates and methyl acrylate to afford ring nitrogen substituted products. The 3-amino, 4-ethoxy analog participates in a self condensation with KOH to form bis-thiadiazolopyrazine oxide dipotassium salt. Alkylation of this with benzyl bromide afforded a dibenzyl derivative with the benzyl groups attached to the central pyrazine nitrogens. Alkylaminothiadiazole oxides cyclized with the diethoxy derivatives to produce similar tricyclic compounds. These tricyclic bis sulfoxides formed diastereomers, indicating that the sulfur is pyramidal and the two forms are stable, i.e. there is no sulfur inversion at room temperature.