Facile Synthesis of Polysubstituted Oxazoles via A Copper-Catalyzed Tandem Oxidative Cyclization

被引:168
作者
Wan, Changfeng
Zhang, Jintang
Wang, Sujing
Fan, Jinmin
Wang, Zhiyong [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Soft Matter Chem, Hefei 230026, Peoples R China
关键词
SP(3) C-H; BOND; DIAZONAMIDE; ACTIVATION; ANNULATION; ARYLATION; ALCOHOLS; PHENOLS; AMIDES; ROUTE;
D O I
10.1021/ol100688c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly efficient synthesis of polysubstituted oxazoles was developed via a copper-catalyzed tandem oxidative cyclization. The desired products can be obtained from readily available starting materials under mild conditions. This is an attractive alternative method for the synthesis of oxazole derivatives.
引用
收藏
页码:2338 / 2341
页数:4
相关论文
共 54 条
[1]   A recyclable copper(II) catalyst for the annulation of phenols with 1,3-dienes [J].
Adrio, Luis A. ;
Hii, King Kuok .
CHEMICAL COMMUNICATIONS, 2008, (20) :2325-2327
[2]   Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids [J].
Basle, Olivier ;
Li, Chao-Jun .
ORGANIC LETTERS, 2008, 10 (17) :3661-3663
[3]   Copper catalyzed oxidative alkylation of sp3 C-H bond adjacent to a nitrogen atom using molecular oxygen in water [J].
Basle, Olivier ;
Li, Chao-Jun .
GREEN CHEMISTRY, 2007, 9 (10) :1047-1050
[4]   Copper-mediated selective oxidation of a C-H bond [J].
Boldron, C ;
Gamez, P ;
Tooke, DM ;
Spek, AL ;
Reedijk, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) :3585-3587
[5]   Modulating the reactivity of α-isocyanoacetates:: Multicomponent synthesis of 5-methoxyoxazoles and furopyrrolones [J].
Bonne, Damien ;
Dekhane, Mouloud ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2485-2488
[6]   Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds [J].
Borduas, Nadine ;
Powell, David A. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) :7822-7825
[7]   A concise and flexible total synthesis of (-)-diazonamide A [J].
Burgett, AWG ;
Li, QY ;
Wei, Q ;
Harran, PG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (40) :4961-4966
[8]   Solid-phase rhodium carbenoid reactions: An N-H insertion route to a diverse series of oxazoles [J].
Clapham, B ;
Spanka, C ;
Janda, KD .
ORGANIC LETTERS, 2001, 3 (14) :2173-2176
[9]   Iterative oxazole assembly via α-chloroglycinates:: Total synthesis of (-)-muscoride A [J].
Coqueron, PY ;
Didier, C ;
Ciufolini, MA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) :1411-1414
[10]   N-H insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1,3-azoles [J].
Davies, JR ;
Kane, PD ;
Moody, CJ .
TETRAHEDRON, 2004, 60 (18) :3967-3977