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Reactivity of Cyanogen towards N ‐Substituted Sulfamides: Synthesis of 1,2,5‐Thiadiazole 1,1‐Dioxide Derivatives
Author(s) -
Alkorta Ibon,
Arán Vicente J.,
Dávila Elena,
Ruiz José R.,
Stud Manfred
Publication year - 1989
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198919890282
Subject(s) - chemistry , cyanogen , tautomer , reactivity (psychology) , hydrolysis , cycloaddition , medicinal chemistry , amino acid , sulfamide , combinatorial chemistry , organic chemistry , catalysis , biochemistry , alternative medicine , pathology , medicine
The acid‐catalyzed cycloaddition of N ‐substituted sulfamides 1a–f with cyanogen affords 2‐substituted 4‐amino‐2,3‐dihydro‐3‐imino‐1,2,5‐thiadiazole 1,1‐dioxides 5a–f which, in turn, could be easily hydrolyzed to give the corresponding 3‐oxo derivatives 2a–f by acid treatment. Direct spectral evidence of amino – imino tautomerism in aminothiadiazole 1,1‐dioxide derivatives has been observed for the first time in compounds 5 .