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The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction
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- Maneeporn Puripat
- Nanoscience and Technology Program, Graduate School, Chulalongkorn University, Bangkok 10330, Thailand
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- Romain Ramozzi
- Fukui Institute for Fundamental Chemistry (FIFC), Kyoto University, Kyoto 606-8103, Japan
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- Miho Hatanaka
- Fukui Institute for Fundamental Chemistry (FIFC), Kyoto University, Kyoto 606-8103, Japan
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- Waraporn Parasuk
- Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand
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- Vudhichai Parasuk
- Nanoscience and Technology Program, Graduate School, Chulalongkorn University, Bangkok 10330, Thailand
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- Keiji Morokuma
- Fukui Institute for Fundamental Chemistry (FIFC), Kyoto University, Kyoto 606-8103, Japan
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Description
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.
Journal
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- The Journal of Organic Chemistry
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The Journal of Organic Chemistry 80 (14), 6959-6967, 2015-06-24
American Chemical Society (ACS)