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

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: [phone]; e-mail: [e-mail]] and are available on request quoting the deposition number CCDC 824124.