The Biginelli Reaction Is a Urea-Catalyzed Organocatalytic Multicomponent Reaction

Maneeporn Puripat, Romain Ramozzi, Miho Hatanaka, Waraporn Parasuk, Vudhichai Parasuk, Keiji Morokuma

Research output: Contribution to journalArticle

43 Citations (Scopus)

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. (Chemical Presented)

Original languageEnglish
Pages (from-to)6959-6967
Number of pages9
JournalJournal of Organic Chemistry
Volume80
Issue number14
DOIs
Publication statusPublished - 2015 Jul 17
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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