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

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 thi...

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Bibliographic Details
Published in:Synthetic communications 2005-12, Vol.35 (23), p.3055-3064
Main Authors: Bonacorso, Helio G., Costa, Michelle B., Lopes, Itamar S., Oliveira, Marlí R., Drekener, Roberta L., Martins, Marcos A. P., Zanatta, Nilo, Flores, Alex F. C.
Format: Article
Language:English
Subjects:
cycloalkenes
pyrimidines
pyrimidinones
Quinazolines
quinazolinones
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Summary: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.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397910500278818