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Facile synthesis of model 1,4-dihydro-1H-1,3,4-benzotriazepin-5-ones

✍ Scribed by Bassam A. Abu Thaher; Jalal A. Zahra; Mustafa M. El-Abadelah

Publisher: Journal of Heterocyclic Chemistry
Year: 2002
Tongue: English
Weight: 48 KB
Volume: 39
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570390508

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✦ Synopsis

Abstract

2‐Aminobenzoic acid reacts readily, in the presence of triethylamine, with hydrazonoyl chlorides (5a‐c) (precursors of the reactive nitrile imine 1,3‐dipolar species) to afford high yields of the corresponding acyclic amidrazone adducts (6a‐c). The latter adducts undergo, in THF in presence of 1,1‐carbonyldiimida‐zole, smooth intramolecular cyclization involving the activated carboxyl and the NH‐ termini to deliver unequivocally the respective dihydro‐1,3,4‐benzotriazepin‐5‐ones (7a‐c).

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