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The complex reaction of acetohydrazides with unsaturated diketones: Alternative cyclizations to 1,2-diazepin-3-ones and pyrazolo[3,4-b]pyridines

✍ Scribed by Alonso, Paloma ;Martín-León, Nazario ;Quinteiro, Margarita ;Seoane, Carlos ;Soto, José L.

Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 646 KB
Volume: 1990
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1990199001158

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✦ Synopsis

Abstract

The reaction of 2‐cyanoacetohydrazide (1) and 2‐(ethoxycarbonyl)acetohydrazide (26) with unsaturated 1,3‐diketones leading with moderate yields to 1,2‐diazepinones (3, 23, 24) and pyrazolo[3,4‐b]pyridines (5, 15, 20, 25) together with the corresponding acetohydrazones have been studied. The reaction course depends on the temperature and the relative reactivity of the carbonyl groups of the starting materials. When one of these carbonyl groups is less reactive (benzoyl or ethoxycarbonyl groups), the reaction does not yield diazepinones but only pyrazolo[3,4‐b]pyridines and/or acetohydrazones.

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