Author/Authors :
Herrera, Antonio Departamento de Química Orgánica - Facultad de Ciencias Químicas - Universidad Complutense, E-28040 Madrid, Spain , Martínez-Alvarez, Roberto Departamento de Química Orgánica - Facultad de Ciencias Químicas - Universidad Complutense, E-28040 Madrid, Spain , Chioua, Mourad Departamento de Química Orgánica - Facultad de Ciencias Químicas - Universidad Complutense, E-28040 Madrid, Spain , Chioua, Rachid Département de Chimie - Université Abdelmalek Essaâdi - Faculté des Sciences, Tétouan, Morocco , Almy, John Department of Chemistry - California State University, Stanislaus, Turlock, CA 95382, USA , Sánchez, Angel CAI de RMN - Facultad de Ciencias Químicas - Universidad Complutense, E-28040 Madrid, Spain
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.
Keywords :
quinazolines , tetrahydroquinazolines , diels-alder reaction , Pyrimidine ortho-quinodimethanes
