Diels-Alder Reactions of Pyrimidine o-Quinodimethanes: Stereochemistry and Applications to the Synthesis of Tetrahydro- and Quinazoline Derivatives

Title: Diels-Alder Reactions of Pyrimidine o-Quinodimethanes: Stereochemistry and Applications to the Synthesis of Tetrahydro- and Quinazoline Derivatives

Volume: 3 Issue: 9

Author(s): Antonio Herrera, Roberto Martinez-Alvarez, Mourad Chioua, Rachid Chioua, John Almy and Angel Sanchez

Affiliation:

Keywords: Pyrimidine ortho-quinodimethanes, diels-alder reaction, tetrahydroquinazolines, quinazolines

Abstract: The Diels-Alder reactions of the ortho-quinodimethane (o-QDM) thermally generated from 2,4- diphenylciclobutapyrimidine with the dienophiles diethyl maleate, diethyl fumarate and dimethyl acetylenedicarboxylate have been investigated. The reaction afforded 5,6,7,8-tetrahydroquinazoline and quinazoline derivatives. While diethyl maleate formed a mixture of cis- and trans-adducts, diethyl fumarate gave only the trans-adduct. The reaction with methyl acetylenedicarboxylate formed a mixture of 5,8- dihydroquinazoline and quinazoline derivatives.

Cite this article as:

Herrera Antonio, Martinez-Alvarez Roberto, Chioua Mourad, Chioua Rachid, Almy John and Sanchez Angel, Diels-Alder Reactions of Pyrimidine o-Quinodimethanes: Stereochemistry and Applications to the Synthesis of Tetrahydro- and Quinazoline Derivatives, Letters in Organic Chemistry 2006; 3 (9) . https://dx.doi.org/10.2174/157017806778699955