Regioselective synthesis of novel substituted pyrazolo[1,5-a]pyrimidines under solvent-free conditions

被引：65

作者：

Quiroga, Jairo ^{[1
]}

Portilla, Jaime ^{[2
]}

Abonia, Rodrigo ^{[1
]}

Insuasty, Braulio ^{[1
]}

Nogueras, Manuel ^{[3
]}

Cobo, Justo ^{[3
]}

机构：

[1] Univ Valle, Heterocycl Cpds Res Grp, Dept Chem, Cali 25360, Colombia

[2] Univ Los Andes, Bioorgan Cpds Res Grp, Dept Chem, Bogota, Colombia

[3] Univ Jaen, Dept Inorgan & Organ Chem, Jaen 23071, Spain

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 43期

关键词：

5-amino-1H-pyrazole; 3-benzoyl-2-methyl-4H-chromen-4-one; pyrazolo[15-a]pyrimidine; solvent-free reaction;

D O I：

10.1016/j.tetlet.2008.08.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 6-(2-hydroxybenzoyl)-5-methyl-7-phenylpyrazolo[1,5-a]pyrimidines 5 have been synthesized directly by the solvent-free reaction between 5-amino-1H-pyrazoles 1 and 3-benzoyl-2-methyl-4H-chromen-4-one 4. This solvent-free reaction proceeds in a regiospecific fashion by intramolecular opening of the gamma-pyrone ring in a Michael-type reaction, that followed by cyclization via nucleophilic attack of endocyclic pyrazole nitrogen toward benzoyl group gives the pyrazolo[1,5-a]pyrimidines 5. The use of this method affords high yields in short reaction times. (C) 2008 Published by Elsevier Ltd.

引用

页码：6254 / 6256

页数：3

共 25 条

[1]

BASINSKI W, 1983, POL J CHEM, V57, P471

[2]

Chiu G., 2006, PCT Int. Appl., Patent No. [2006130673, WO 2006130673]

[3] Microwave-assisted protocols for the expedited synthesis of pyrazolo[1,5-a] and [3,4-d]pyrimidines [J].

Daniels, R. Nathan ;

Kim, Kwangho ;

Lebois, Evan P. ;

Muchalski, Hubert ;

Hughes, Mary ;

Lindsley, Craig W. .

TETRAHEDRON LETTERS, 2008, 49 (02) :305-310

[4] Versatile templates for the development of novel kinase inhibitors: Discovery of novel CDK inhibitors [J].

Dwyer, Michael P. ;

Paruch, Kamil ;

Alvarez, Carmen ;

Doll, Ronald J. ;

Keertikar, Kerry ;

Duca, Jose ;

Fischmann, Thierry O. ;

Hruza, Alan ;

Madison, Vincent ;

Lees, Emma ;

Parry, David ;

Seghezzi, Wolfgang ;

Sgambellone, Nicole ;

Shanahan, Frances ;

Wiswell, Derek ;

Guzi, Timothy J. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (22) :6216-6219

[5] Cyclization reactions of 5-aminopyrazoles with β-ketoesters, enamines and β-keto anilides:: New synthetic routes to pyrazolo[1,5-a]pyrimidine derivatives [J].

El-Taweel, FMA ;

Abu Elmaati, TM .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2002, 49 (06) :1051-1055

[6] CHEMISTRY OF PYRAZOLOPYRIMIDINES [J].

ELNAGDI, MH ;

ELMOGHAYAR, MRH ;

ELGEMEIE, GEH .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1987, 41 :319-376

[7]

Feurer A., 2004, PCT Int. Appl., Patent No. [WO2004009589, 2004009589]

[8] Synthesis of 3-(1H-benzimidazol-2-yl)-5-isoquinolin-4-ylpyrazolo[1,2-b]pyridine, a potent cyclin dependent kinase 1 (CDK1) inhibitor [J].

Huang, Shenlin ;

Lin, Ronghui ;

Yu, Yang ;

Lu, Yanhua ;

Connolly, Peter J. ;

Chiu, George ;

Li, Shengjian ;

Emanuel, Stuart L. ;

Middleton, Steven A. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (05) :1243-1245

[9] Novel pyrazolo[1,5-a]pyrimidines as c-Src kinase inhibitors that reduce IKr channel blockade [J].

Mukalyama, Harunobu ;

Nishimura, Toshihiro ;

Kobayashi, Satoko ;

Komatsu, Yoshimitsu ;

Kikuchi, Shinji ;

Ozawa, Tomonaga ;

Kamada, Noboru ;

Ohnota, Hideki .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (02) :909-921

[10]

PORTILLA J, 2006, ACTA CRYSTALLOGR E, V62, P3195

← 1 2 3 →