Synthesis and reactivity of some amino‐substituted 1,2,5‐thiadiazole 1,1‐dioxides
1988; Wiley; Volume: 1988; Issue: 4 Linguagem: Inglês
10.1002/jlac.198819880406
ISSN0170-2041
AutoresVicente J. Arán, José Rafael Ruiz, E. DAVILA, Ibón Alkorta, M. Stud,
Tópico(s)Synthesis and Reactions of Organic Compounds
ResumoAbstract The acid‐catalyzed cyclizing addition of sulfamide to cyanogen yielded 3,4‐diamino‐1,2,5‐thiadiazole 1,1‐dioxide ( 2 ), from which through amino‐exchange reactions, the substituted compounds 3, 4 , and 5 could be derived. The unsubstituted amino groups of compounds 2 and 3 were easily hydrolyzed by basic treatment; the former afforded the 4‐amino‐3‐oxothiadiazole 8 or the dipotassium salt 6 depending on the conditions, and the latter, 4‐amino‐3‐oxo‐1,2,5‐thiadiazoles 1 . Alternative syntheses of compounds 1a, b , and 8 by hydrogenolysis of the corresponding 2‐benzyl derivatives are also reported.
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