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Synthesis 2011(5): 783-793  
DOI: 10.1055/s-0030-1258421
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Diverse Directions of Heterocyclizations Involving Derivatives of 5-Aminopyrazoles and N-Arylmaleimides

Roman V. Rudenkoa, Sergey A. Komykhov*a, Sergey M. Desenkoa,b, Vladimir I. Musatova, Oleg V. Shishkina, Irina S. Konovalovaa, Elena V. Vashchenkoa, Valentin A. Chebanov*a
a State Scientific Institution ‘Institute for Single Crystals’ of National Academy of Sciences of Ukraine, Lenin Ave. 60, 61001 Kharkiv, Ukraine
Fax: +38(57)3410273; e-Mail: komykhov@isc.kharkov.com; e-Mail: chebanov@isc.kharkov.com;
b Karazin Kharkiv National University, Svobody sq., 4, 61077 Kharkiv, Ukraine
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Publikationsverlauf

Received 5 November 2010
Publikationsdatum:
03. Februar 2011 (online)

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Abstract

Heterocyclization reactions between derivatives of 5-aminopyrazoles and N-arylmaleimides were studied and it was established that several directions are possible. Cyclizations involving 1,3-unsubstituted 5-aminopyrazoles yielded mixtures of two regioisomeric compounds, pyrazolo[1,5-a]pyrimidine-7-carboxamides and pyrazolo[3,4-b]pyridine-4-carboxamides. Reactions of 4-substituted 5-aminopyrazoles in boiling acetic acid or N,N-dimethylformamide in most cases gave pyrazolo[1,5-a]pyrimidine-7-carboxamides as the sole product. The treatment of 1-substituted 5-aminopyrazoles with maleimides possesses high selectivity only in N,N-dimethylformamide yielding pyrazolopyridines while in acetic acid the formation mixtures with pyrrolopyrazolones is observed. The key intermediates of the reaction studied were isolated and discussed.

Key words

heterocycle - N-arylmaleimide - 5-aminopyrazole - pyrazolopyridine - pyrazolopyrimidine

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11

The final atomic coordinates and crystallographic data for molecule 7l have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam.ac.uk] and is available on request quoting the deposition number CCDC 792559.