CC BY-NC-ND 4.0 · SynOpen 2020; 04(04): 71-83
DOI: 10.1055/s-0040-1707304
paper

Synthesis and Crystal Structures of 4,5-Dihydroimidazo[1,5-b]pyrazol-6-ones

,
María Vera
,
Bruno Martiz
,
Francisco Ródenas
,
,
,
Delia Bautista
The authors acknowledge the financial support of the Fundación Séneca of the Comunidad Autónoma de la Región de Murcia (project 19249/PI/14).


Abstract

The synthesis of previously unattainable 2,5-disubstituted 4,5-dihydroimidazo[1,5-b]pyrazol-6-ones has been developed. Electrochemical reductions of readily available 2,2,2-trichloroethylideneacetophenones were followed by reaction with hydrazine, leading to 3-aryl-5-dichloromethyl-2-pyrazolines. These were treated with isocyanates to obtain the corresponding aminocarbonyl derivatives, which were found to be able to form an otherwise almost inaccessible imidazo[1,5-b]pyrazole ring system via a one-step reaction involving internal condensation followed by hydrogen chloride elimination and aromatization. The molecular­ structures of 2-(4-methylphenyl)-5-tosyl-4,5-dihydro­imidazo[1,5-b]pyrazol-6-one, 5-dichloromethyl-N-(4-chlorophenyl)-4,5-dihydro-3-p-tolylpyrazole-1-carboxamide, and 5-(4-bromophenyl)-2-p-tolyl-4,5-dihydroimidazo[1,5-b]pyrazol-6-one were determined by X-ray crystallographic analysis.

Supporting Information



Publication History

Received: 13 July 2020

Accepted after revision: 27 August 2020

Publication Date:
07 October 2020 (online)

© 2020. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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