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Synthesis 2003(2): 0227-0232
DOI: 10.1055/s-2003-36827
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Functionalized 4H-Pyran and Cyclohexanone Derivatives via Three-Component Reactions of Dimethyl Acetonedicarboxylate, Aromatic Aldehydes­, and Malononitrile

Dieter Heber*a, Edmont V. Stoyanov*b
Department of Pharmaceutical Chemistry, University of Kiel, Gutenbergstr. 76, 24118 Kiel, Germany
Fax: +49(431)8801118; e-Mail: dheber@pharmazie.uni-kiel.de;
Department of Industrial Pharmacy, Faculty of Pharmacy, Medical University of Sofia, Dunav 2, 1000 Sofia, Bulgaria
e-Mail: estoyanov@yahoo.com;
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Publication History

Received 30 September 2002
Publication Date:
22 January 2003 (online)

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Abstract

Dependent on the reaction time, the three-component condensation of dimethyl acetonedicarboxylate (1), aromatic aldehydes 2, and malononitrile (3) gives rise to 4H-pyran derivatives 5 after reflux for 15 min. Moreover, using excess of benzaldehyde and prolonged heating for 150 min afforded multifunctional cyclohexanone derivatives 8. Different substitution patterns in the phenyl nucleus of 8 can be achieved by condensation of 4H-pyran derivatives 5 with benzaldehydes 2.

Key words

heterocycles - carbocycles - Michael additions - rearrangements - cyclizations - condensation