The reaction of malononitrile with chalcone: a controversial chemical process

Pedro Victory; José I. Borrell; Anton Vidal-Ferran; Carlos Seoane; José L. Soto

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

The reaction of malononitrile with chalcone: a controversial chemical process

Pedro Victory^*
, José I. Borrell
, Anton Vidal-Ferran
, Carlos Seoane
, José L. Soto

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

71 Citations (Scopus)

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.

Original language	English
Pages (from-to)	5375-5378
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	39
DOIs	https://doi.org/10.1016/S0040-4039(00)92390-6
Publication status	Published - 23 Sept 1991

Keywords

2-aminoisophthalonitrile
3-cyanopyridine
4H-pyran
Versatile Michael addition
hexasubstituted cyclohexanol

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10.1016/S0040-4039(00)92390-6

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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.",

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AU - Victory, Pedro

AU - Borrell, José I.

AU - Vidal-Ferran, Anton

AU - Seoane, Carlos

AU - Soto, José L.

PY - 1991/9/23

Y1 - 1991/9/23

N2 - 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.

AB - 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.

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KW - 3-cyanopyridine

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KW - Versatile Michael addition

KW - hexasubstituted cyclohexanol

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The reaction of malononitrile with chalcone: a controversial chemical process

Abstract

Keywords

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