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Issue 37, 2013
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Synthesis of novel pyrazole-based heterocycles via a copper(ii)-catalysed domino annulation

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Abstract

Pyrazole-based β-aminonitriles and β-amino-carbaldehydes as bifunctional building blocks are introduced in a facile copper(II)-catalysed one-pot domino generation of multiple N-containing heterobi- and tricycles. This streamlined synthetic approach permits easy access to novel pyrazole-fused imidazo- and pyrimido[1,2-c]pyrimidinones and to pyrazolo[3,4-d]pyrimidinone species with isolated yields up to 90%. The present study also reveals a unique amine–isocyanate coupling promotion via copper(II)-based catalytic activation.

Graphical abstract: Synthesis of novel pyrazole-based heterocycles via a copper(ii)-catalysed domino annulation

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Supplementary files

Article information


Submitted
04 Jun 2013
Accepted
17 Jul 2013
First published
25 Jul 2013

Org. Biomol. Chem., 2013,11, 6320-6327
Article type
Paper

Synthesis of novel pyrazole-based heterocycles via a copper(II)-catalysed domino annulation

M. Gyuris, L. G. Puskás, G. K. Tóth and I. Kanizsai, Org. Biomol. Chem., 2013, 11, 6320
DOI: 10.1039/C3OB41146J

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