Nucleophilic Addition of CH Acids to αβ-unsaturated Aldehydes and Ketones

Yanovskaya, L. A.; Kryshtal, G. V.; Kul'ganek, V. V.

doi:10.1070/rc1984v053n08abeh003096

Cited by 31 publications

(6 citation statements)

References 3 publications

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“…1 Synthesis of 3,6 and 1,6 dihydropyrimidine derivatives (6a-c) (general procedure). 1 Synthesis of 3,6 and 1,6 dihydropyrimidine derivatives (6a-c) (general procedure).…”

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confidence: 99%

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Reaction of aromatic aldehydes with β-dicarbonyl compounds in a catalytic system: Piperidinium acetate-1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid

2005

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Condensation of aromatic (heteroaromatic) aldehydes with 1,3 dicarbonyl com pounds under the 1 butyl 3 methylimidazolium tetrafluoroborate ([Bmim][BF 4 ]) ionic liq uid-piperidinium acetate catalytic system (0.2 equiv. of each component) in the absence of a solvent affords, depending on the structures of the reagents, 2 arylidene derivatives of methyl acetoacetate and acetylacetone, diethyl 2,4 bis(trifluoroacetyl) 3 phenylpentanedioate, or di methyl 2 aryl 4 hydroxy 6 oxocyclohexane 1,3 dicarboxylates. The reactions of the resulting 2 arylidene derivatives with O methylisourea in the [Bmim] [BF 4 ] ionic liquid produced me thyl 2 methoxy 4 methyl 6 aryldihydropyrimidine 5 carboxylates and 1 (2 methoxy 4 me thyl 6 phenyldihydropyrimidin 5 yl)ethanone (mixtures of 3,6 and 1,6 dihydro isomers), which were transformed into the corresponding 3,4 dihydropyrimidin 2(1H ) one derivatives.

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“…1 Synthesis of 3,6 and 1,6 dihydropyrimidine derivatives (6a-c) (general procedure). 1 Synthesis of 3,6 and 1,6 dihydropyrimidine derivatives (6a-c) (general procedure).…”

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confidence: 99%

“…1 Synthesis of 3,4 dihydropyrimidin 2(1H ) one derivatives 7a-c (general procedure). The yield was 78%, oil.…”

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confidence: 99%

Reaction of aromatic aldehydes with β-dicarbonyl compounds in a catalytic system: Piperidinium acetate-1-butyl-3-methylimidazolium tetrafluoroborate ionic liquid

2005

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“…Nucleophilic additions to conjugated unsaturated systems have been the subject of numerous studies and have been comprehensively reviewed . The influence of the nature of the nucleophile, temperature, and additives on the mode of the reaction (1,2- or 1,4-addition) has been of major interest.…”

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confidence: 99%

1,2- vs 1,4-Addition of Acylbenzotriazoles to α,β-Unsaturated Aldehydes and Ketones. A Novel Route to 3-Alkyl-4,6-diaryl-3,4-dihydropyran-2-ones

Katritzky

Denisko

2002

J. Org. Chem.

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“…Consequently, with all things being equal, localization of the charge at the nucleophilic group and decreasing of the HOMO (highest occupied molecular orbital) energy favor addition of the nucleophile to the carbonyl group. On the other hand, increasing of the charge delocalization and increasing of the HOMO energy causes orbital control of the 1,4-addition [14,17].…”

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confidence: 99%