2-methyl-7-substituted pyrazolo[1,5-a]pyrimidines: highly regioselective synthesis and bromination

The reaction of 3-amino-5-methyl-1H-pyrazole with 1,1,1-trichloro-4-alkoxy-3-alken-2-ones [CCl3C(O)CH=C(R¹)OR, where R¹/R = H/Me, Me/Et, Et/Me, Pr/Et, Bu/Me, iso-Bu/Me] or β-dimethylaminovinyl ketones [R²C(O)CH=CHNMe2, where R² = Ph, Ph-4-Me, Ph-4-F, Ph-4-Cl, Ph-4-Br, Ph-4-NO2, fur-2-yl, thien-2-yl, pyrrol-2-yl, pyrid-2-yl], in acetic acid under reflux for 16 hours, furnished highly regioselective the halomethylated pyrazolo[1,5-a]pyrimidines and aryl[heteroaryl]pyrazolo[1,5-a]pyrimidines, respectively. A protocol for the bromination reaction at the 3-position pyrazolo[1,5-a]pyrimidines also was investigated.

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Bibliographic Details
Main Authors: Martins,Marcos A. P., Scapin,Elisandra, Frizzo,Clarissa P., Rosa,Fernanda A., Bonacorso,Helio G., Zanatta,Nilo
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2009
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000200003
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