Triazines and related products. Part XIV. Decomposition of 1,2,3-benzotriazin-4(3H)-ones in the presence of reactive methylene systems

M S S Siddiqui, M. F G Stevens

Research output: Contribution to journalArticle

Abstract

In the presence of ß?-unsaturated esters, 1,2,3-benzotriazin-4(3H)-one (1) is thermally transformed into the quinazolino[3,2-c][1,2,3]benzotriazinone (13), which then undergoes cleavage of the N(2)-N(3) bond in the triazine ring to afford the quinazolinylphenylhydrazones (14). The initial step in the reaction probably involves a nucleophilic attack of one molecule of the triazinone (1) at the reactive 4-position of another molecule. 3-Alkyl-and 3-aralkyl-1,2,3-benzotriazin-4(3H)-ones are all stable in boiling ethyl cyanoacetate, but the 3-arylbenzotriazinones undergo thermal heterolysis of the N(2)-N(3) bond, followed by reaction with the ester, to yield phenylcarbamoylphenylhydrazones.

Original languageEnglish
Pages (from-to)2482-2486
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - 1974

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