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

Reactions of 5(4H)-Oxazolones with Wittig-Horner Reagents: Novel Synthesis of Dioxopyrrolidinephosphonates and Phosphonoalkanoates with Anticipated Schistosomicidal Activity

2008 ◽  
Vol 63 (10) ◽  
pp. 1211-1218 ◽  
Author(s):  
Leila S. Boulosa ◽  
Mona H.N. Arsanious ◽  
Ewies F. Ewies ◽  
Fatem Ramzy
Keyword(s):  
Reaction Mechanisms ◽  
Sodium Ethoxide ◽  
Sodium Hydride ◽  
Biological Evaluation ◽  
Novel Synthesis ◽  
New Compounds ◽  
Sodium Alkoxide

Abstract4-Benzylidene-2-phenyl-5(4H)-oxazolones react with Wittig-Horner reagents in the presence of alcoholic sodium alkoxide to give novel dioxopyrrolidinephosphonates, diethyl [3-(benzoylamino)- 1-cyano-2-oxo-4-phenylbut-3-en-1-yl]phosphonate and phosphonoalkenoate derivatives. Both the phosphonate adducts and the ester products were also isolated from the reaction of oxazolones with triethyl phosphonoacetate using alcoholic sodium ethoxide and/or sodium hydride as a base. Possible reaction mechanisms are considered, and the structural assignments are based on analytical and spectroscopic results. The biological evaluation of the new compounds is reported.

6,11-Dihydrodibenzo[b,e]thiepin-11-thiol and 11-acetic acid derivatives; Some 2-methyl-6,11-dihydrodibenzo[b,e]thiepins; Synthesis and pharmacological screening

1979 ◽  
Vol 44 (9) ◽  
pp. 2689-2701 ◽  
Author(s):  
Vladimír Valenta ◽  
František Kvis ◽  
Jiří Němec ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Zinc Chloride ◽  
Local Anaesthetic ◽  
Diethyl Malonate ◽  
Acetyl Derivative ◽  
Cardiovascular Activity ◽  
Starting Compound ◽  
Pharmacological Screening ◽  
Neurotropic Effects ◽  
Sodium Amide

11-Chloro-6,11-dihydrodibenzo[b,e]thiepin was transformed via the isothiourea V to the thiol IV which was used for the synthesis of aminoalkyl sulfides VII and VIII and of the methylpiperazide X. The same starting compound was used for alkylating diethyl malonate and via the intermediates XIV and XV, 6,11-dihydrodibenzo[b,e]thiepin-11-acetic acid (XVI) was obtained, which was converted to the methylpiperazide XVIII. Oxime XIX and 2-diethylaminoethylimine XX were prepared from 2-methyldibenzo[b,e]thiepin-11(6H)-one (II). Reduction of the ketone II afforded 2-methyl-6,11-dihydrodibenzo[b,e]thiepin (XII) giving by treatment with sodium amide and 3-dimethylaminopropyl chloride the amine XXIII. In the reaction of 6,11-dihydrodibenzo[b,e]thiepin-11-ol with sodium amide and 3-dimethylaminopropyl chloride, C-alkylation took place in addition to the expected etherification resulting in the diamine XXII. Reaction of phthalide with 4-aminothiophenol gave the acid XXIV which was transformed to the 3-dimethylaminopropyl ester XXV and N-acetyl derivative XXVI. Compound XXVI was cyclized with zinc chloride to the ketone III. Some of the compounds prepared exhibit structurally less specific peripheral and vegetative neurotropic effects (local anaesthetic, spasmolytic) and cardiovascular activity (antiarrhytmic).

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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