Palladium-catalyzed oxidative C-H/C-H cross-couplings of thiazolo [5,4-d]pyrimidine with aromatic (hetero)cycles

被引：10

作者：

Yang, Sheng-Wei ^{[1
,2
]}

Su, Ye-Xiang ^{[1
,2
]}

Sun, Li-Ping ^{[1
,2
]}

机构：

[1] China Pharmaceut Univ, Jiangsu Key Lab Drug Design & Optimizat, Nanjing 210009, Jiangsu, Peoples R China

[2] China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China

来源：

TETRAHEDRON | 2014年 / 70卷 / 23期

关键词：

Palladium-catalyzed; Cross-coupling; Thiazolo[5,4-d]pyrimidine; C-H activation; ARYL BOND FORMATION; COORDINATED PHOSPHINES; DIRECT ARYLATION; FUNCTIONALIZATION; OLEFINS; INDOLES; ACETATE;

D O I：

10.1016/j.tet.2014.03.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Pd(II)-catalyzed dehydrogenative cross-coupling reaction of thiazolo[5,4-d]pyrimidine with unactivated (hetero)arenes via C-H bond activation was achieved. This protocol provides a straightforward and operationally simple method for the synthesis of 2-arylsubstituted thiazolo[5,4-d]pyrimidines of interest in pharmaceutical sciences. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3730 / 3734

页数：5

共 44 条

[1] Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].

Ackermann, Lutz .

CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877

[2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[4] Efficient palladium-catalyzed direct arylation of azines and diazines using ligand-free conditions [J].

Baso, Luca ;

Beccalli, Egle M. ;

Borsini, Elena ;

Broggini, Gianluigi .

TETRAHEDRON, 2009, 65 (17) :3486-3491

[5] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].

Brasche, Gordon ;

Garcia-Fortanet, Jorge ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2008, 10 (11) :2207-2210

[6] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[7] THIAZOLOPYRIMIDINES [J].

CHILDRESS, SJ ;

MCKEE, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (08) :3862-3864

[8] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[9] Gold-Catalyzed Ethynylation of Arenes [J].

de Haro, Teresa ;

Nevado, Cristina .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1512-+

[10] C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls [J].

Dwight, Timothy A. ;

Rue, Nicholas R. ;

Charyk, Dagmara ;

Josselyn, Ryan ;

DeBoef, Brenton .

ORGANIC LETTERS, 2007, 9 (16) :3137-3139

← 1 2 3 4 5 →