2-Methyl-7-Substituted Pyrazolo[1,5-a]pyrimidines: Highly Regioselective Synthesis and Bromination

被引：33

作者：

Martins, Marcos A. P. ^{[1
]}

Scapin, Elisandra ^{[2
]}

Frizzo, Clarissa P. ^{[1
]}

Rosa, Fernanda A. ^{[1
]}

Bonacorso, Helio G. ^{[1
]}

Zanatta, Nilo ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos, BR-97105900 Santa Maria, RS, Brazil

[2] Univ Fed Tocantins, Lab Quim, Coordenacao Engn Ambiental, Palmas, TO, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2009年 / 20卷 / 02期

关键词：

pyrimidines; pyrazoles; pyrazolo[1,5-a]pyrimidines; enones; bromination; SOLVENT-FREE CONDITIONS; COMBINATORIAL LIBRARIES; REGIOSPECIFIC SYNTHESIS; HETEROCYCLIC SYNTHESIS; RECEPTOR LIGANDS; EFFICIENT METHOD; INHIBITORS; MICROWAVE; PYRAZOLO<1,5-A>PYRIMIDINES; 5-AMINOPYRAZOLES;

D O I：

10.1590/S0103-50532009000200003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 3-amino-5-methyl-1H-pyrazole with 1,1,1-trichloro-4-alkoxy-3-alken-2-ones [CCl(3)C(O) CH= C(R(1))OR, where R(1)/R = H/Me, Me/Et, Et/Me, Pr/Et, Bu/Me, iso-Bu/Me] or beta-dimethylaminovinyl ketones [R(2)C(O)CH=CHNMe(2), where R(2) = Ph, Ph-4-Me, Ph-4-F, Ph-4-Cl, Ph-4-Br, Ph-4-NO(2), 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.

引用

页码：205 / 213

页数：9

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