A one-pot process for the microwave-assisted synthesis of 7-substituted pyrazolo[1,5-a] pyrimidine

被引：18

作者：

Bassoude, Ibtissam ^{[1
,2
]}

Tber, Zahira ^{[1
]}

Essassi, El Mokhtar ^{[2
,3
]}

Guillaumet, Gerald ^{[1
]}

Berteina-Raboin, Sabine ^{[1
]}

机构：

[1] Univ Orleans, Inst Chim Organ & Analyt, UMR CNRS 7311, F-45067 Orleans, France

[2] Univ Mohammed V Agdal, Fac Sci, Lab Chim Organ Heterocycl URAC 21, Rabat 10100, Morocco

[3] RABAT Design Ctr, Ctr Composites & Nanocomposites, MAScIR, Rabat 10100, Morocco

来源：

RSC ADVANCES | 2016年 / 6卷 / 04期

关键词：

CATALYZED ALPHA-ARYLATION; ESTROGEN-RECEPTOR LIGANDS; CARBONYL-COMPOUNDS; PALLADIUM; DISCOVERY; OPTIMIZATION; ANTAGONISTS; ACETAMIDES; INHIBITORS; KETONES;

D O I：

10.1039/c5ra23417d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient synthesis of 7-substituted pyrazolo[1,5-a] pyrimidines using a one-pot, two-step process via Pd-catalyzed direct CH-arylation followed by a saponification-decarboxylation reaction is reported. Compared to the classical method (Negishi coupling), this new procedure has the advantages of convenient manipulation, short reaction times, excellent yields and the use of commercially available and relatively non-toxic compounds.

引用

页码：3301 / 3306

页数：6

共 49 条

[1] Synthesis and SAR of a new series of COX-2-selective inhibitors:: Pyrazolo[1,5-α]pyrimidines [J].

Almansa, C ;

de Arriba, AF ;

Cavalcanti, FL ;

Gómez, LA ;

Miralles, A ;

Merlos, M ;

García-Rafanell, J ;

Forn, J .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (03) :350-361

[2] Catalyst- and Base-Controlled Site-Selective sp2 and sp3 Direct Arylation of 5,7-Dimethyl-2-phenylpyrazolo[1,5-a]pyrimidine Using Aryl Bromides [J].

Bassoude, Ibtissam ;

Berteina-Raboin, Sabine ;

Massip, Stephane ;

Leger, Jean-Michel ;

Jarry, Christian ;

Essassi, El Mokhtar ;

Guillaumet, Gerald .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (13) :2572-2578

[3] One-step reaction leading to new pyrazolo[1,5-a]pyrimidines by condensation of 2-pyrone with 5(3)-amino-3(5)-arylpyrazoles [J].

Bassoude, Ibtissam ;

Berteina-Raboin, Sabine ;

Leger, Jean-Michel ;

Jarry, Christian ;

Essassi, El Mokhtar ;

Guillaumet, Gerald .

TETRAHEDRON, 2011, 67 (12) :2279-2286

[4] One-pot sequential Cu-catalyzed reduction and Pd-catalyzed arylation of silyl enol ethers [J].

Chae, JH ;

Yun, JS ;

Buchwald, SL .

ORGANIC LETTERS, 2004, 6 (26) :4809-4812

[5] Optimization of 3-phenylpyrazolo[1,5-a[pyrimidines as potent corticotropin-releasing factor-1 antagonists with adequate lipophilicity and water solubility [J].

Chen, C ;

Wilcoxen, KM ;

Huang, CQ ;

McCarthy, JR ;

Chen, T ;

Grigoriadis, DE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (14) :3669-3673

[6] Pyrazolo[1,5-a]pyrimidines:: Estrogen receptor ligands possessing estrogen receptor β antagonist activity [J].

Compton, DR ;

Sheng, SB ;

Carlson, KE ;

Rebacz, NA ;

Lee, IY ;

Katzenellenbogen, BS ;

Katzenellenbogen, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) :5872-5893

[7] Pyrazolo[1,5-a]pyrimidines as estrogen receptor ligands:: defining the orientation of a novel heterocyclic core [J].

Compton, DR ;

Carlson, KE ;

Katzenellenbogen, JA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (22) :5681-5684

[8] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[9] Discovery of 4H-pyrazolo[1,5-a]pyrimidin-7-ones as potent inhibitors of hepatitis C virus polymerase [J].

Deng, Yongqi ;

Shipps, Gerald W., Jr. ;

Wang, Tong ;

Popovici-Muller, Janeta ;

Rosner, Kristin E. ;

Siddiqui, M. Arshad ;

Duca, Jose ;

Cooper, Alan B. ;

Cable, Michael .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (18) :5363-5367

[10] 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

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