Chemoselectivity of Multicomponent Condensations of Barbituric Acids, 5-Aminopyrazoles, and Aldehydes

Abstract

Multicomponent cyclocondensations between 5-aminopyrazoles, barbituric acids, and aromatic aldehydes under conventional thermal heating, microwave irradiation, or ultrasonic irradiation were studied and the temperature regime was found to be the main factor in controlling their chemoselectivity. At high temperatures the starting materials react in two different ways yielding pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidines or their dihydro analogues depending on the nature of the N-substituent in the 5-aminopyrazole. Treatment at room temperature results in a new four-component reaction giving previously undisclosed heterocyclic compounds, 4,6-diaryl-1,4,6,7-tetrahydro-2′H-spiro[pyrazolo[3,4-b]pyridine-5,5′-pyrimidine]s. Facile multipurpose three-component selective procedures to new spiroheterocycles are proposed.

Key words

heterocycles - multicomponent reactions - selectivity - ultrasonication - microwave-assisted synthesis

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19

The final atomic coordinates, and crystallographic data for molecules 4a and 6h have been deposited with 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 numbers CCDC 706772 for 4a and CCDC 706773 for 6h.