The Effects of Different Catalysts, Substituted Aromatic Aldehydes on One-Pot Three-Component Biginelli Reaction

Author(s): Zong-liang Liu*, Ren-mei Zhang, Ye Liu, Yan Guo, Qing-guo Meng.

Journal Name: Current Organic Synthesis

Volume 16 , Issue 1 , 2019

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Abstract:

Aim and Objective: The Biginelli reaction, first reported in 1893, is one great example of the important multicomponent reactions reported from 1893. Under the same conditions, the influence of the common catalysts on the yield of the Biginelli reaction was investigated.

Materials and Method: To a round-bottom flask equipped with a spherical condenser were added 1,3- dicarbonyl compound (1.0 eq), urea (1.45 eq), aromatic aldehyde (1.0 eq), catalyst and methanol. The mixture was heated at reflux for 16 h. After cooling off, the mixture was filtered and washed with cold methanol to give DHPMs. Reaction solution was further purified by recrystallization with petroleum ether and ethyl acetate. Six catalytic systems, different 1,3-dicarbonyl compounds and different substituted aromatic aldehydes with varied substitutions are described for the Biginelli reaction. An analysis was also performed to study the factors that affect the yield of the reaction.

Results: When 1,3-dicarbonyl compound was ethyl acetoacetate, the CuCl/ conc.H2SO4 system gave the highest yield (90.5%). While when acetoacetamide was used, the yields of DHPMs in presence of PTSA/conc. HCl, conc. HCl or FeCl3•6H2O were all over 90%. Nine DHPMs with different substituents were obtained.

Conclusion: The Lewis acid or mixed catalyst had no significant advantage over a single protonic acid as catalyst. Conc. HCl as the catalyst was found to be the most effective condition for the preparation of DHPMs. The aromatic aldehyde with weak electron-withdrawing substituent such as Br resulted in the best yield.

Keywords: Multicomponent reactions, Biginelli reaction, catalysts, synthetize, substituents, reaction conditions.

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Article Details

VOLUME: 16
ISSUE: 1
Year: 2019
Page: [181 - 186]
Pages: 6
DOI: 10.2174/1570179416666181122100405
Price: $58

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