Synthesis and Diels - Alder cycloadditions of exo-imidazolidin-2-one dienes

Rafael Bautista, Pablo Bernal, Rafael Herrera, Blanca M. Santoyo, J. Miguel Lazcano-Seres, Francisco Delgado, Joaquín Tamariz

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

(Figure presented) An efficient and versatile synthesis of novel exo-imidazolidin-2-one dienes is described. This involves the base-assisted condensation/cyclization cascade reaction of the monoimino derivatives of diacetyl with a series of isocyanates. This methodology enables preparation of symmetrical dienes, as long as the substrates have the same N substituent. Moreover, use of different N-substituted starting materials leads to formation of nonsymmetrical dienes. The reactivity of these dienes was evaluated in Diels - Alder reactions, showing a high reactivity.

Original languageEnglish
Pages (from-to)7901-7911
Number of pages11
JournalJournal of Organic Chemistry
Volume76
Issue number19
DOIs
StatePublished - 7 Oct 2011

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