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New heterocycles from tetrazines and oxadiazoles
Author(s) -
Chavez David E.,
Parrish Damon A.
Publication year - 2009
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.7
Subject(s) - chemistry , nucleophile , oxadiazole , reactivity (psychology) , tetrazine , nucleophilic substitution , medicinal chemistry , combinatorial chemistry , base (topology) , nucleophilic aromatic substitution , organic chemistry , catalysis , medicine , mathematical analysis , alternative medicine , mathematics , pathology
The reactivity of 3,4‐diamino‐1,2,5‐oxadiazole ( 2 ) toward nucleophilic substitution of 3,6‐bis(3,5‐dimethylpyrazol‐1yl)‐1,2,4,5‐tetrazine ( 1 ) was studied. A new class of high nitrogen heterocyclic systems was prepared. It was determined that 3,4‐diamino‐1,2,5‐oxadiazole did not display the required nucleophilicity to be reactive. However, the anion of 3,4‐diamino‐1,2,5‐oxadiazole, prepared by treatment with strong base, was sufficiently reactive to act as a nucleophile. J. Heterocyclic Chem., (2009).