The Condensation of Ethyl Acetoacetate to Isodehydroacetic Acid and Ethyl Ester

1951 ◽  
Vol 73 (7) ◽  
pp. 3531-3533 ◽  
Author(s):  
Richard H. Wiley ◽  
Newton R. Smith
Keyword(s):  
Ethyl Ester ◽  
Ethyl Acetoacetate

scholarly journals Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives

2018 ◽  
Vol 14 ◽  
pp. 2529-2536 ◽  
Author(s):  
Nicholas G Jentsch ◽  
Jared D Hume ◽  
Emily B Crull ◽  
Samer M Beauti ◽  
Amy H Pham ◽  
...  
Keyword(s):  
Sodium Hydroxide ◽  
Ethyl Ester ◽  
Ethyl Acetoacetate ◽  
Hiv Integrase ◽  
Isatoic Anhydride ◽  
Aminobenzoic Acids ◽  
Substituted Quinolines ◽  
Anthranilic Acids ◽  
Hydroxyacetic Acid

A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially available 2-aminobenzoic acids. In step 1, the anthranilic acids are smoothly converted to isatoic anhydrides using solid triphosgene in THF. In step 2, the anhydride electrophiles are reacted with the sodium enolate of ethyl acetoacetate, generated from sodium hydroxide, in warm N,N-dimethylacetamide resulting in the formation of substituted quinolines. A degradation–build-up strategy of the ethyl ester at the 3-position allowed for the construction of the α-hydroxyacetic acid residue required for the synthesis of key arylquinolines involved in an HIV integrase project.

PRODUCTION AND PROPERTIES OF 2,3-BUTANEDIOL: XXIII. CONDENSATION OF THE ISOMERIC 2,3-BUTANEDIOLS WITH ETHYL ACETOACETATE

1947 ◽  
Vol 25b (5) ◽  
pp. 423-429 ◽  
Author(s):  
A. C. Neish
Keyword(s):  
Hydrochloric Acid ◽  
Ethyl Ester ◽  
Ethyl Acetoacetate ◽  
Free Acid ◽  
Butyl Ester ◽  
Melting Points ◽  
First Time

levo-2,3-Butanediol will condense with ethyl acetoacetate in the presence of hydrochloric acid to give the ethyl ester of levo-2,4,5-trimethyl-2-carboxymethyl-1,3-dioxacyclopentane (I) (yield 48%) from which the free acid may be obtained. If p-toluenesulphonic acid is used as the catalyst and the condensation is carried out in boiling butanol with continuous removal of water, the butyl ester of (I) is obtained (yield 87%). Compounds described for the first time are levo-, dl-, and meso-2,4,5-trimethyl-2-carboxymethyl-1,3-dioxacyclopentanes, their n-butyl and p-bromophenacyl esters (melting points 74.5°, 76°, and 76 °C., respectively) and the ethyl ester of the levo-isomer.

Synthesis of Dihydropyrimidinones (DHPMs) and Hexahydro Xanthene Catalyzed by 1,4-Diazabicyclo [2.2.2] Octane Triflate Under Solvent-Free Condition

2019 ◽  
Vol 16 (5) ◽  
pp. 776-786 ◽  
Author(s):  
Deepa ◽  
Geeta D. Yadav ◽  
Mohd J. Aalam ◽  
Pooja Chaudhary ◽  
Surendra Singh
Keyword(s):  
Ethyl Acetoacetate ◽  
Biginelli Reaction ◽  
Solvent Free ◽  
Efficient Catalyst ◽  
Solvent Free Condition ◽  
Solvent Free Conditions ◽  
Xanthene Derivatives ◽  
Different Temperatures ◽  
Flash Column Chromatography ◽  
Biginelli Condensation

Objective:DABCO salts were evaluated as catalysts for the Biginelli reaction between 4- methoxybenzaldehyde, urea and ethyl acetoacetate under solvent-free conditions. 1,4-Diazabicyclo [2.2.2] octane triflate was found to be a simple, inexpensive, highly efficient catalyst for Biginelli reaction for a variety aromatic aldehyde with urea and ethyl acetoacetate at 80°C afforded corresponding 3,4-dihydropyrimidinones in 50-99% yields after 30-120 minutes. 1,3-Cyclohexadione was used in place of ethyl acetoacetate in the absence of urea this methodology is giving hexahydro xanthene derivatives in good to excellent yields after 3-4 hours.Methods:DABCO salt 4 (5 mol%), 4-methoxybenzaldehyde (0.73 mmol) and urea (0.73 mmol) were stirred for 10 minutes at 80°C, then ethyl acetoacetate (1.5 equiv.) was added and reaction mixture was stirred at 80°C for specified time. The resulting solution was stirred continuously and progress of the reaction was followed by TLC. The crude reaction mixture was purified by flash column chromatography on silica gel (hexane/ethyl acetate (1:2)) to give pure desired product.Results:Reaction conditions of the Biginelli reaction were optimized using 4-methoxybenzaldehyde (0.73 mmol), urea (0.73 mmol), and ethyl acetoacetate (5 equiv.) as model substrates catalyzed by 1,4-Diazabicyclo [2.2.2] octane triflate (5 mol%) in a different solvents, screening of different catalysts and different temperatures. Neat condition was found to be the best for the Biginelli condensation and corresponding 3,4- dihydropyrimidinones was obtained in good to excellent yields. When the reaction was carried out with benzaldehyde derivatives and cyclohexane-1,3-dione in place of ethyl acetoacetate in the absence of urea, solely corresponding hexahydro xanthene derivatives were obtained in 61-91% yields.Conclusion:In conclusion, we have applied salts of 1,4-Diaza-bicyclo [2.2.2] octane as catalysts in the Biginelli condensation and corresponding 3,4-dihydropyrimidinones were obtained in 50- 99% yields under solvent free conditions. This methodology is having advantages like simple work-up; low loading of catalyst and reaction was performed at moderate temperature under solvent-free conditions.

Synthesis and Antibacterial Screening of Some Pyrazole Derivatives Catalyzed by Cetyltrimethylammoniumbromide (CTAB)

2020 ◽  
Vol 17 ◽  
Author(s):  
Ravi Bansal ◽  
Pradeep K. Soni ◽  
Neha Gupta ◽  
Sameer S. Bhagyawant ◽  
Anand K. Halve
Keyword(s):  
Hydrazine Hydrate ◽  
Ethyl Acetoacetate ◽  
Aromatic Aldehydes ◽  
Pyrazole Derivatives ◽  
Phenyl Hydrazine ◽  
One Pot ◽  
Antibacterial Screening ◽  
Water As Solvent ◽  
Substituted Pyrazoles ◽  
Sulfinic Esters

Aims: In this article we have developed an eco-friendly one-pot multi-component reaction methodology was employed for the green synthesis of functionalized pyrazole derivatives viz cyclo-condensation of aromatic aldehydes, ethyl acetoacetate and phenyl hydrazine and/or hydrazine hydrate in the presence of cetyltrimethylammoniumbromide (CTAB) at 90°C temperature in aqueous medium. Method: In the present protocol we developed a green method for the synthesis of functionalized pyrazole derivatives through one-pot, multi-component cyclo-condensation of aromatic aldehydes, phenyl hydrazine or hydrazine hydrate and ethyl acetoacetate using cetyltrimethylammoniumbromide (CTAB) as a catalyst in water as solvent. Our methodology confers advantages such as short reaction time, atom economy, purification of product without using column chromatographic and hazardous solvent. The reaction is being catalyzed by cetyltrimethylammoniumbromide (CTAB) and thus products are formed under the green reaction conditions. Results: Initially the reaction of benzaldehyde and phenylhydrazine with ethyl acetoacetate was carried out in water at room temperature in the absence of the catalyst; no product was obtained after 24 h (Table 1 entry 1). When the reaction was carried out using L-proline as catalyst in ethanol at 70°C the yield of product was 20. Conclusion: This research not only provides a green and efficient method for the synthesis of sulfinic esters but also shows new applications of electrochemistry in organic synthesis. We consider that this green and efficient synthetic protocol used to prepare sulfinic esters will have good applications in future. In conclusion, we have developed successfully a green and efficient one-pot multi-component methodology for the synthesis of substituted pyrazoles using CTAB as a catalyst in water as solvent with excellent yields. Purifications of compounds were achieved without the use of traditional chromatographic procedures. This methodology has advantages of operational simplicity, clean reaction profiles and relatively broad scope which make it more attractive for the diversity oriented synthesis of these heterocyclic libraries. In this methodology we suggest the further alternative possibility for formation of substituted pyrazoles. The compound 7h can be used as an anticancer drug in pharma industry.

Polymeric Micelles for the Delivery of Diclofenac and Its Ethyl Ester Derivative

2016 ◽  
Vol 4 (2) ◽  
pp. 109-119 ◽  
Author(s):  
Hanan Al-Lawati ◽  
Mohammad R. Vakili ◽  
Fakhreddin Jamali ◽  
Afsaneh Lavasanifar
Keyword(s):  
Ethyl Ester ◽  
Polymeric Micelles ◽  
Ester Derivative
Sign in / Sign up

Export Citation Format

Share Document