Alkyl Cyanoacetic Acids.

Hessler, John C.

doi:10.1021/ja02261a020

Cited by 7 publications

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“…equilibrium with small amounts of its valence tautomer, 7,7-dicyanocycloheptatriene (33). 1v l 2 Ionization of this intermediate would produce cyanotropylium cyanide (34a) which might recombine at C-3 to give the observed product, 3,7-dicyanocycloheptatriene (3).…”

Section: Discussionmentioning

confidence: 99%

The Cycloheptatriene-Norcaradiene System. II.¹ Reactions of 7,7-Dicyanonorcaradienes

Ciganek¹

1967

J. Am. Chem. Soc.

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Section: Discussionmentioning

confidence: 99%

The Cycloheptatriene-Norcaradiene System. II.¹ Reactions of 7,7-Dicyanonorcaradienes

Ciganek¹

1967

J. Am. Chem. Soc.

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“…Phenyl-4-quinazolylacetonitrile. To a solution of sodio ethyl phenylcyanoacetate prepared from 1.44 g. of sodium and 13.35 g. of ethyl phenylcyanoacetate (18) in 200 ml. of pure dioxane (17) was added 10.5 g. of 4-chloroquinazoline.…”

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confidence: 99%

The Acid Catalyzed Cleavage of 4-Quinazolylmalonic Ester and Related Compounds to 4-Quinazolone

Elderfield¹,

Serlin²

1951

J. Org. Chem.

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Malonic esters and their substituted derivatives undergo a well-known variety of cleavages under the influence of acidic or basic reagents. As representative of these cleavages the following examples may be cited. When a malonic ester is SUMMARY 1. 4-QuinazoIyImaIonic ester and related compounds have been prepared and found to cleave to 4-quinazolone in acid solution.2. Diethyl ethyl-(2,6-dimethyl-4-pyrimidyl)malonate and ethyl (2,6-dimethyl-4-pyrimidyl)cyanoacetate have been prepared. These compounds undergo hydrolysis and decarboxylation in acid.New York 27, N. Y.

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The Alkylation of Esters and Nitriles

2011

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This chapter is concerned with the reactions of metal salts (enolates) of active methylene compounds with alkylating agents such as alkyl halides to produce allyl derivatives. The first example of this reaction is found in the literature when Geuther prepared ethyl alpha‐ethyl acetoacetate by the reaction of the sodium enolate of ethyl acetoacetate with ethyl iodide. The active methylene compounds considered in the chapter include malonic esters, cyanoacetic esters, malonitriles, monocarboxylic esters and mononitriles. These classes of compounds are characterized by the presence of one or more acidic hydrogen atoms attached to carbon. Only C‐alkylation has been observed with active methylene compounds and are discussed here. Several alternative methods for the preparation of alkyl and aryl derivatives of carboxylic esters and nitriles have been included.

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Alkyl Cyanoacetic Acids.

Cited by 7 publications

References 0 publications

The Cycloheptatriene-Norcaradiene System. II.¹ Reactions of 7,7-Dicyanonorcaradienes

The Cycloheptatriene-Norcaradiene System. II.¹ Reactions of 7,7-Dicyanonorcaradienes

The Acid Catalyzed Cleavage of 4-Quinazolylmalonic Ester and Related Compounds to 4-Quinazolone

The Alkylation of Esters and Nitriles

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Alkyl Cyanoacetic Acids.

Cited by 7 publications

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The Cycloheptatriene-Norcaradiene System. II.1 Reactions of 7,7-Dicyanonorcaradienes

The Cycloheptatriene-Norcaradiene System. II.1 Reactions of 7,7-Dicyanonorcaradienes

The Acid Catalyzed Cleavage of 4-Quinazolylmalonic Ester and Related Compounds to 4-Quinazolone

The Alkylation of Esters and Nitriles

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The Cycloheptatriene-Norcaradiene System. II.¹ Reactions of 7,7-Dicyanonorcaradienes

The Cycloheptatriene-Norcaradiene System. II.¹ Reactions of 7,7-Dicyanonorcaradienes