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1,2,5‐Selenadiazoles. Synthesis and properties
Author(s) -
Shealy Y. Fulmer,
Clayton Joe D.
Publication year - 1967
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570040117
Subject(s) - chemistry , pyrimidine , amide , reagent , ring (chemistry) , antifungal , hydrolysis , amine gas treating , alkyl , cleavage (geology) , hydrazine (antidepressant) , primary (astronomy) , stereochemistry , aqueous solution , carboxylic acid , organic chemistry , biochemistry , medicine , physics , geotechnical engineering , dermatology , astronomy , fracture (geology) , engineering
Abstract 4‐Amino‐1, 2, 5‐selenadiazole‐3‐carboxylic acid and 4‐amino‐1, 2, 5‐selenadiazole‐3‐carboxamides have been prepared by ring‐cleavage of [1, 2, 5]selenadiazolo[3, 4‐ d ]pyrimidin‐7(6 H )‐one by basic reagents. The primary amide (III), as well as an N ‐alkyl amide, may be produced by the action of a primary amine. Hydrazine reductively cleaves the selenadiazole ring. The preparation of similar 4‐ureido derivatives by ring‐cleavage of [1,2,5]selenadiazolo[3, 4‐ d ]pyrimidine‐5, 7(4 H , 6 H )‐dione has been demonstrated with two examples. N ‐Butyl‐4‐ureido‐1, 2, 5‐selenadiazole‐3‐carboxamide is easily hydrolyzed in aqueous base to the corresponding acid, and it has been shown that this reaction proceeds by way of [1, 2, 5]selenadiazolo[3,4‐ d ]pyrimidine‐5, 7 (4 H , 6 H )‐dione. The 4‐amino‐1, 2, 5‐selenadiazole‐3‐carboxylic acid derivatives have marked cytotoxic, antibacterial, and antifungal activity.