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4-Aryldihydropyrimidines via the Biginelli Condensation: Aza-Analogs of Nifedipine-Type Calcium Channel Modulators
Molecules 1998, 3(1), 10-15; doi:10.3390/30100010
Article

Synthesis and Intramolecular [4+2] Cycloaddition Reactions of 4-Pyridazinecarbonitriles with Alkyne Side Chains

 and *
Institute of Pharmaceutical Chemistry, University of Vienna, A-1090 Vienna, Austria
* Author to whom correspondence should be addressed.
Received: 15 October 1997 / Accepted: 19 November 1997 / Published: 25 January 1998
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Abstract

The preparation of a series of new 3-(alkynyl-X)-substituted 4-pyridazinecarbonitriles 2-5 (X = O, NH) is described. The compounds are shown to undergo thermally induced intramolecular Diels-Alder reactions with inverse electron demand, affording the fused benzonitriles 6-8. Incorporation of a 1,2-phenylene unit into the side chain, as in the case of compounds 10 and 13, results in a more favorable conformation of the dienophilic substructure and thus to a pronounced acceleration of the [4+2] cycloaddition reaction.
Keywords: [4+2] Cycloaddition; inverse-electron-demand Diels-Alder reaction; 4-pyridazinecarbonitriles [4+2] Cycloaddition; inverse-electron-demand Diels-Alder reaction; 4-pyridazinecarbonitriles
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Fülep, G.; Haider, N. Synthesis and Intramolecular [4+2] Cycloaddition Reactions of 4-Pyridazinecarbonitriles with Alkyne Side Chains. Molecules 1998, 3, 10-15.

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