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Cyclocondensation of 3‐amino‐2‐hydrazino‐4(3 H )‐pyrimidinones with dimethyl acetylenedicarboxylate. Formation of 1‐amino‐2,6‐dihydro‐2,6‐dioxo‐1 H ‐pyrimido[1,2‐ b ][1,2,4]triazine‐3‐acetic acid esters
Author(s) -
Bitha Panayota,
Hlavka Joseph J.,
Lin YangI
Publication year - 1988
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.5570250308
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , pyrimidinones , acetic acid , hydrazone , amino acid , organic chemistry , medicinal chemistry , cycloaddition , catalysis , biochemistry
[(1‐Amino‐6‐hydroxy‐2(1 H )‐pyrimidinylidene)hydrazone]butanedioic acid dimethyl esters 3 , formed from 3‐amino‐2‐hydrazino‐4(3 H )‐pyrimidinones and dimethyl acetylenedicarboxylate in acetic acid at room temperature, underwent a facile, thermal rearrangement to 1‐amino‐2,6‐dihydro‐2,6‐dioxo‐1 H ‐pyrimido‐[1,2‐ b ]‐[1,2,4]triazine‐3‐acetic acid methyl esters 6 in hot acetic acid.