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

Elena A. Muravyova; Svetlana V. Shishkina; Vladimir I. Musatov; Irina V. Knyazeva; Oleg V. Shishkin; Sergey M. Desenko; Valentin A. Chebanov

doi:10.1055/s-0028-1088024

PAPER

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

Elena A. Muravyova, Svetlana V. Shishkina, Vladimir I. Musatov, Irina V. Knyazeva, Oleg V. Shishkin, Sergey M. Desenko, Valentin A. Chebanov*
State Scientific Institution ‘Institute for Single Crystals’ of National Academy of Sciences of Ukraine, Lenin Ave. 60, 61001 Kharkiv, Ukraine
Fax: +38(57)3409343; e-Mail: chebanov@isc.kharkov.com;

Abstract

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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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