Synthesis of Tetrahydro‐2(1H)quinazolinones, Cyclopenta[d]‐2(1H)pyrimidinones, and Their Thioxo Analogs from 2‐Trifluoroacetyl‐1‐methoxycycloalkenes

Abstract

A series of six (8)‐alkyl‐4‐trifluoromethyl‐5,6,7,8‐tetrahydro‐2(1H)quinazolinones, 4‐trifluoromethyl‐cyclopenta[d]‐2(1H)pyrimidinones, and their thioxo analogs from the reaction of five β‐alkoxyvinyl trifluoromethyl ketones, derived from alkylated cyclohexanones and cyclopentanone with urea and thiourea, is reported. The reactions were carried out in a single step in propan‐2‐ol as solvent and boron trifluoride diethyl etherate as catalyst in 18–65% yield.

Keywords:

• Quinazolines
• quinazolinones
• pyrimidines
• pyrimidinones
• cycloalkenes

Acknowledgments

The authors are thankful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for financial support. Fellowships from Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) (to M. R. Oliveira and M. B. Costa) and Fundação de Apoio à Ciência e Tecnologia (FATEC) (to R. L. Drekener) are also acknowledged.