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1,2,4‐Triazoles from formic acid‐Induced rearrangement of 6‐(Phenylhydrazino)uracils
Author(s) -
Wright G. E.
Publication year - 1977
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.5570140438
Subject(s) - chemistry , formic acid , uracil , decarboxylation , ring (chemistry) , formylation , nitrogen atom , medicinal chemistry , triazole , sigmatropic reaction , stereochemistry , organic chemistry , catalysis , dna , biochemistry
The structure of a rearrangement product of 6‐(phenylhydrazino)uracil + formic acid has been proved to be 1‐phenyl‐3‐carboxamidomethyl‐1,2,4‐triazole: hydrolysis of this compound and thermal decarboxylation of the intermediate acid gave the known 1‐phenyl‐3‐methyl‐1,2,4‐triazole. Yields of triazoles from substituted 6‐(phenylhydrazino)uracils follow inversely yields of pyrimidoindoles derived from Fischer‐type cyclization [ J. Heterocyclic Chem. , 13 , 539 (1976)]. The lack of formation of a triazole from 3‐methyl‐6‐(phenylhydrazino)uracil suggests that an intermediate in this rearrangement, ie ., that resulting from formylation of the anilino nitrogen atom followed by intramolecular cyclization involving the uracil 1‐nitrogen atom, must undergo conjugate elimination of water to generate the triazole ring.