The Decomposition of Acylated Malonic Esters for the Preparation of β-Keto Esters

Kaneda, Akira; Itoh, Nobuhiro; Sudo, Rokuro

doi:10.1246/bcsj.40.228

Bulletin of the Chemical Society of Japan

1967

DOI: 10.1246/bcsj.40.228

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The Decomposition of Acylated Malonic Esters for the Preparation of β-Keto Esters

Akira Kaneda¹,

Nobuhiro Itoh²,

Rokuro Sudo³

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Cited by 7 publications

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“…In contrast to the "alkylative" malonic synthesis of carboxylic acids, strongly basic conditions are to be avoided since acyl cleavage occurs here at the more reactive ketone carbonyl (8). In addition to the rather harsh procedure of Riegel and Lilienfeld (9), several successful monodecarboethoxylations in dilute aqueous acidic medium are known (10,11). The most widely used procedure is, however, a simple aqueous hydrolysis related to the Merwein cleavage of diethyl alkylmalonates to carboxylic acids (12).…”

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3-Ketoesters by malonic synthesis

Pollet¹

1983

J. Chem. Educ.

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mentioning

confidence: 99%

3-Ketoesters by malonic synthesis

Pollet¹

1983

J. Chem. Educ.

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Synthesis and insecticidal activity of novel 1,3,4-oxadiazolin-5-one and pyrazolin-5-one derivatives

et al. 1999

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A series of novel 2-(2,4,6-trisubstituted phenyl)-1,3,4-oxadiazolin-5-one derivatives and 3-(2,4,6-trichlorophenyl)pyrazolin-5-one derivatives were synthesized and evaluated for insecticidal activity. It was found that a moderately bulky alkyl group, such as a tert-butyl group, on the heterocyclic ring, and a triýuoromethyl group on the benzene ring were optimal substituents on the molecule. The oxygen atom in the oxadiazoline ring was essential for insecticidal activity. Of the compounds assayed, 4-tert-butyl-2-(2,6-dichloro-4-triýuoromethylphenyl)-1,3,4-oxadiazolin-5-one gave the highest activity against Nephtotettix cincticeps, with an value of 0.51 mg litre-1. LC 50 1999 Society of Chemical Industry (

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Synthesis and insecticidal activity of nitroguanidine derivatives

et al. 1999

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Nitroguanidine derivatives with thiazol‐5‐ylmethyl moieties were prepared and their insecticidal activities against homopterous pests were tested. New synthetic routes for 2‐chloro‐5‐chloromethylthiazole from 2,3‐dichloro‐1‐propene and for substituted nitroguanidines from S‐methyl‐N‐nitroisothiourea were established. Biological evaluation led to a novel insecticide (E)‐1‐(2‐chlorothiazol‐5‐ylmethyl)‐3‐methyl‐2‐nitroguani dine (TI‐435) which has a broad activity spectrum and is under development. ©1999 Society of Chemical Industry

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The Decomposition of Acylated Malonic Esters for the Preparation of β-Keto Esters

Cited by 7 publications

References 3 publications

3-Ketoesters by malonic synthesis

3-Ketoesters by malonic synthesis

Synthesis and insecticidal activity of novel 1,3,4-oxadiazolin-5-one and pyrazolin-5-one derivatives

Synthesis and insecticidal activity of nitroguanidine derivatives

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