Biginelli reaction

The Biginelli reaction is a multiple-component chemical reaction that creates 3,4-dihydropyrimidin-2(1H)-ones from ethyl acetoacetate, an aryl aldehyde (such as benzaldehyde), and urea . It is named for the Italian chemist Pietro Biginelli.

References

 

First application of hexaaquaaluminium(III) tetrafluoroborate as a mild, recyclable, non-hygroscopic acid catalyst in organic synthesis: a simple and efficient protocol for the multigram scale synthesis of 3,4-dihydropyrimidinones by Biginelli reaction

TetrahedronVolume 66, Issue 198 May 2010Pages 3463-3471
Mladen Litvić, Ivana Večenaj, Zrinka Mikuldaš Ladišić, Marija Lovrić, Vladimir Vinković, Mirela Filipan-Litvić

 

A piperidinium triflate catalyzed Biginelli reaction
TetrahedronVolume 66, Issue 1617 April 2010
Pages 2987-2994
Chennan Ramalingan, Su-Jung Park, In-Sook Lee, Young-Woo Kwak

 

An improved synthesis of Biginelli-type compounds via phase-transfer catalysis 

Tetrahedron LettersVolume 50, Issue 2417 June 2009Pages 2889-2892
Bahar Ahmed, Riaz A. Khan, Habibullah, Manoj Keshari

 

Calcium fluoride: an efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)thione: an improved high yielding protocol for the Biginelli reaction
Tetrahedron LettersVolume 50, Issue 1913 May 2009
Pages 2222-2224
S. Chitra, K. Pandiarajan

 
Highly Enantioselective Organocatalytic Biginelli and Biginelli-Like Condensations: Reversal of the Stereochemistry by Tuning the 3,3′-Disubstituents of Phosphoric Acids

Nan Li, Xiao-Hua Chen, Jin Song, Shi-Wei Luo, Wu Fan and Liu-Zhu Gong

J. Am. Chem. Soc.2009131 (42),pp 15301–15310

 

Highly Enantioselective Organocatalytic Biginelli Reaction

J. Am. Chem. Soc.2006128 (46), pp 14802–14803

Xiao-Hua Chen, Xiao-Ying Xu, Hua Liu, Lin-Feng Cun, and Liu-Zhu Gong

 

Concise Synthesis of Guanidine-Containing Heterocycles Using theBiginelli Reaction

Bradley L. Nilsson and Larry E. Overman

J. Org. Chem.200671 (20), pp 7706–7714

 

Two Novel Diastereoselective Three-Component Reactions of Alkenes or 3,4-Dihydro-(2H)-pyran with Urea/Thiourea−Aldehyde Mixtures: [4 + 2] Cycloaddition vs Biginelli-Type Reaction

Yulin Zhu, Shenlin Huang, Jieping Wan, Lei Yan, Yuanjiang Pan, and Anxin Wu

Org. Lett.20068 (12), pp 2599–2602


 

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