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

Autor:	Puripat M; †Nanoscience and Technology Program, Graduate School, Chulalongkorn University, Bangkok 10330, Thailand.; ‡Fukui Institute for Fundamental Chemistry (FIFC), Kyoto University, Kyoto 606-8103, Japan., Ramozzi R; ‡Fukui Institute for Fundamental Chemistry (FIFC), Kyoto University, Kyoto 606-8103, Japan., Hatanaka M; ‡Fukui Institute for Fundamental Chemistry (FIFC), Kyoto University, Kyoto 606-8103, Japan., Parasuk W; §Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand., Parasuk V; †Nanoscience and Technology Program, Graduate School, Chulalongkorn University, Bangkok 10330, Thailand.; ∥Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand., Morokuma K; ‡Fukui Institute for Fundamental Chemistry (FIFC), Kyoto University, Kyoto 606-8103, Japan.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2015 Jul 17; Vol. 80 (14), pp. 6959-67. Date of Electronic Publication: 2015 Jun 24.
DOI:	10.1021/acs.joc.5b00407
Abstrakt:	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.
Databáze:	MEDLINE
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