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Synthesis 2011(19): 3161-3167  
DOI: 10.1055/s-0030-1260163
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Comprehensive Study of the Heterocyclizations of N-Arylmaleimides and 6-Aminouracils

Roman V. Rudenkoa, Sergey A. Komykhov*a, Sergey M. Desenkoa,b, Yulia V. Sen’koa, Oleg V. Shishkina,b, Irina S. Konovalovaa, Svetlana V. Shishkinaa, 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
Further Information

Publication History

Received 31 May 2011
Publication Date:
09 August 2011 (online)

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Abstract

Heterocyclization reactions between N-arylmaleimides and 6-aminouracils were studied in detail. It was established that several directions are possible depending on the nature of reaction medium and the substituent character in the uracil component. The synthetic procedure leading to N-phenyl-2,4,7-trioxopyrido[2,3-d]pyrimidine-5-carboxamides in good-to-high yields was developed and key stages of the corresponding reaction were established.

Key words

heterocycles - nucleophilic addition - ring opening - pyridines - pyrroles - annulation - regioselectivity

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15

The final atomic coordinates and crystallographic data for molecule 3j have been deposited at the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk] and are available on request quoting the deposition number CCDC 824124.