Phase-transfer-catalyzed alkylation of ethyl acetoacetate and diethyl malonate

1985 ◽  
Vol 62 (10) ◽  
pp. 907 ◽  
Author(s):  
Douglas L. Thompson ◽  
Perry C. Reeves
Keyword(s):  
Ethyl Acetoacetate ◽  
Phase Transfer ◽  
Diethyl Malonate

Novel Synthesis of 3-Spiroheterocycles-2-methylquinolin-4-one

1993 ◽  
Vol 58 (9) ◽  
pp. 2215-2221 ◽  
Author(s):  
Abd El-Hamid N. Ahmed
Keyword(s):  
Phthalic Anhydride ◽  
Zinc Chloride ◽  
Ethyl Acetoacetate ◽  
Diethyl Malonate ◽  
Novel Synthesis ◽  
Structure Similarity ◽  
New Compounds

2-Methyl[3,1]benzoxazin-4-one (I) is easily accessible , but its chemistry has not been investigated enough. Structure similarity between I and phthalic anhydride encouraged us to investigate the reaction of I with compounds bearing active methylenes namely diethyl malonate, ethyl acetoacetate and acetylacetone in presence of zinc chloride, Thus new compounds II, III and IV were synthesized. Those compounds were used as precursors for the synthesis of various spiroheterocycles.

A 2-methylthio-3,5-diaryl-1,3,4-thiadiazolium cation; its reactions, and further exploration of the chemistry of 2-alkyl-3,5-diaryl-1,3,4-thiadiazolium cations

1987 ◽  
Vol 65 (12) ◽  
pp. 2713-2716 ◽  
Author(s):  
Harold Mastalerz ◽  
Taj Mohammad ◽  
Martin S. Gibson
Keyword(s):  
Nucleophilic Substitution ◽  
Ethyl Acetoacetate ◽  
Diethyl Malonate ◽  
Ring System ◽  
Cationic Dyes ◽  
Substitution Reactions ◽  
Reaction Conditions ◽  
Nucleophilic Substitution Reactions ◽  
Thiadiazole Ring

Activation of a representative 3,5-diaryl-1,3,4-thiadiazole-2-thione by thione S-methylation gives a cation that is readily susceptible to nucleophilic substitution. Reactions with diethyl malonate, ethyl acetoacetate, acetylacetone, cyclopentan-1,3-dione, or 3-ethylrhodanine under basic conditions lead to β,β-disubstituted methine bases and (or) β-substituted methine bases in cases where deacetylation occurs under the reaction conditions. This cation and the 2-alkyl-3,5-diaryl-1,3,4-thiadiazolium cation are convenient sources of a series of neutral and cationic dyes containing the 1,3,4-thiadiazole ring system.

Condensation of Unsaturated SCHIFF Bases with ethyl acetoacetate, diethyl malonate and acetylacetone

1972 ◽  
Vol 314 (1) ◽  
pp. 139-144 ◽  
Author(s):  
A. Sammour ◽  
M. I. B. Selim ◽  
M. M. Nour Eldeen
Keyword(s):  
Schiff Bases ◽  
Ethyl Acetoacetate ◽  
Diethyl Malonate

Condensation reactions of 1,1-dimorpholinoethene and of 1,1-dipiperidinoethene with carbon acids

1987 ◽  
Vol 65 (12) ◽  
pp. 2717-2721 ◽  
Author(s):  
Sham S. Gandhi ◽  
Martin S. Gibson
Keyword(s):  
Michael Addition ◽  
Ethyl Acetoacetate ◽  
Ethyl Cyanoacetate ◽  
Diethyl Malonate ◽  
Condensation Reactions ◽  
Acetyl Group ◽  
Carbon Acids

1,1-Dimorpholinoethene and 1,1-dipiperidinoethene condense with such compounds as malononitrile, ethyl cyanoacetate, cyanoacetamide, and diethyl malonate to give the corresponding β,β-disubstituted enamine, a molecule of morpholine or piperidine being eliminated in the process. Similar reactions with acetylacetone and ethyl acetoacetate proceed with loss of the acetyl group to give the β-substituted enamine. 1,1-Dipiperidinoethene and nitromethane give the β-nitroenamine. Secondary processes of either hydrolysis or further Michael addition and elimination are noted in condensations of 1,1-dimorpholinoethene or 1,1-dipiperidinoethene with cyanoacetamide under more basic conditions.1,1-Dipiperidinoethene is arylated at the 2-position by 2,4-dinitrochlorobenzene.

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