The reaction of malononitrile with chalcone: a controversial chemical process

doi:10.1016/S0040-4039(00)92390-6

Tetrahedron Letters

Volume 32, Issue 39, 23 September 1991, Pages 5375-5378

https://doi.org/10.1016/S0040-4039(00)92390-6 Get rights and content

Abstract

Given the significant discrepancies in the several reported results on the reaction of chalcone (1,3-diphenyl-2-propne-1-one) (1) with malononitrile (2), a careful reinvestigation was carried out. Depending upon the reaction conditions either the open-chain Michael adduct (4), an alkoxypyridine (5), an aminoisophthalonitrile (6) or a cyclohexanol (7) is obtained. However, no 4H-pyran could be isolated from this reaction.

The reinvestigation of the title reaction has shown that only 4, 5, 6 and 7 can be obtained depending on the reaction conditions employed. In no case the corresponding 4 $H$ -pyran was detected.

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Citation Excerpt :
2,6-Dicyanoanilines are typically prepared from (arylidene)malononitriles and (1-arylethylidene)malononitriles in the presence of a base [8,5a]. Other synthetic routes include: reaction of malononitrile and α,β-unsaturated ketones [5c], one-pot tandem reaction of (alkylidene)malononitriles with nitroolefins in the presence of a base [9], reaction of ynones and malononitrile [10], reaction of α-methylene ketones or enamino ketones with malononitrile [11], ringtransformation of functionalized 2H-pyran-2-ones with malononitrile [12], the three-component reaction of aldehydes, ketones and malononitrile under solvent-free conditions [13,5g] or microwave irradiation [3], and reaction between arylidenemalononitriles, dialkyl acetylenedicarboxylates and malononitrile catalyzed by 1-methylimidazole [5f], reactions between nitrostyrenes and excess malononitrile [14]. Due to the interesting chemistry of dicyanoanilines, the development of synthetic methods easily accessible to these useful compounds is desirable.

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The reaction of malononitrile with chalcone: a controversial chemical process

Abstract

Tetrahedron Lett.

An. Quim.