Tetrahedron letters

Efficient synthesis of quinazolinones as intermediates of CNS agents via inverse-electron demand Diels–Alder reaction

ER Bilbao, M Alvarado, CF Masaguer, E Raviña

Index: Bilbao, Estibaliz R.; Alvarado, Mario; Masaguer, Christian F.; Ravina, Enrique Tetrahedron Letters, 2002 , vol. 43, # 19 p. 3551 - 3554

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Citation Number: 23

Abstract

Enaminones undergo inverse electron demand Diels–Alder reaction with 1, 3, 5-triazine, allowing access to functionalised quinazolinones as intermediates in the synthesis of CNS agents. This reaction is highly dependent of the solvent: 1, 3, 5-triazine undergoes single or double [4+ 2] cycloadditions with enaminones, and quinazolinones or acridinediones can be selectively obtained.