Literature DB >> 26066623

The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction.

Maneeporn Puripat1,2, Romain Ramozzi2, Miho Hatanaka2, Waraporn Parasuk3, Vudhichai Parasuk1,4, Keiji Morokuma2.   

Abstract

The recently developed artificial force induced reaction (AFIR) method was applied to search systematically all possible multicomponent pathways for the Biginelli reaction mechanism. The most favorable pathway starts with the condensation of the urea and benzaldehyde, followed by the addition of ethyl acetoacetate. Remarkably, a second urea molecule catalyzes nearly every step of the reaction. Thus, the Biginelli reaction is a urea-catalyzed multicomponent reaction. The reaction mechanism was found to be identical in both protic and aprotic solvents.

Entities:  

Year:  2015        PMID： 26066623     DOI： 10.1021/acs.joc.5b00407

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  6 in total

1.  Design, synthesis, and characterization of (1-(4-aryl)- 1H-1,2,3-triazol-4-yl)methyl, substituted phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates against Mycobacterium tuberculosis.

Authors:  Katharigatta N Venugopala; G B Dharma Rao; Subhrajyoti Bhandary; Melendhran Pillay; Deepak Chopra; Bandar E Aldhubiab; Mahesh Attimarad; Osama Ibrahim Alwassil; Sree Harsha; Koleka Mlisana
Journal:  Drug Des Devel Ther       Date:  2016-08-25       Impact factor: 4.162

2.  Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions.

Authors:  Andreas C Boukis; Baptiste Monney; Michael A R Meier
Journal:  Beilstein J Org Chem       Date:  2017-01-09       Impact factor: 2.883

3.  The new life of traditional water treatment flocculant polyaluminum chloride (PAC): a green and efficient micro-nano reactor catalyst in alcohol solvents.

Authors:  Gang Wang; Pengcheng Hao; Yanping Liang; Yuwang Liang; Wanyi Liu; Jiantong Wen; Xiang Li; Haijuan Zhan; Shuxian Bi
Journal:  RSC Adv       Date:  2021-12-23       Impact factor: 3.361

4.  Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products.

Authors:  Alakbar E Huseynzada; Christian Jelch; Haji Vahid N Akhundzada; Sarra Soudani; Cherif Ben Nasr; Aygun Israyilova; Filippo Doria; Ulviyya A Hasanova; Rana F Khankishiyeva; Mauro Freccero
Journal:  RSC Adv       Date:  2021-02-03       Impact factor: 3.361

5.  Iodonium salts as efficient iodine(iii)-based noncovalent organocatalysts for Knorr-type reactions.

Authors:  Sevilya N Yunusova; Alexander S Novikov; Natalia S Soldatova; Mikhail A Vovk; Dmitrii S Bolotin
Journal:  RSC Adv       Date:  2021-01-22       Impact factor: 3.361

6.  An Efficient, Eco-friendly and Sustainable One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Directly from Alcohols Catalyzed by Heteropolyanion-Based Ionic Liquids.

Authors:  Renzhong Fu; Yang Yang; Xudong Ma; Yu Sun; Jin Li; Hang Gao; Huaxing Hu; Xiaojun Zeng; Jun Yi
Journal:  Molecules       Date:  2017-09-11       Impact factor: 4.411
  6 in total

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