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

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

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 9 , 2006

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

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Article Details

Year: 2006
Page: [703 - 708]
Pages: 6
DOI: 10.2174/157017806778699955
Price: $65

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