Formation of C=N bonds by the release of H2: a new strategy for synthesis of imines and benzazoles

被引：49

作者：

Jin, Xukang ^{[1
]}

Liu, Yuxiao ^{[1
]}

Lu, Qiongqiong ^{[1
]}

Yang, Dejun ^{[1
]}

Sun, Jiangkai ^{[1
]}

Qin, Shuangshuang ^{[1
]}

Zhang, Jingwu ^{[1
]}

Shen, Jiaxuan ^{[1
]}

Chu, Changhu ^{[1
]}

Liu, Renhua ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Dept Chem, Shanghai 200237, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 23期

基金：

国家高技术研究发展计划(863计划); 中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; AEROBIC OXIDATION; CATALYTIC-SYSTEM; HIGHLY EFFICIENT; TERTIARY-AMINES; ACCEPTORLESS DEHYDROGENATION; 2-SUBSTITUTED BENZOXAZOLES; ALCOHOL DEHYDROGENATION; DIRECT CONVERSION; ANTITUMOR;

D O I：

10.1039/c3ob40388b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for synthesis of imines using the approach of release of H-2 has been developed. This oxidant-and acceptor-free Pd/C catalysis protocol is further applied to synthesis of benzoxazoles, benzimidazoles, and benzothiazoles through a one-pot cascade reaction with notably high yields.

引用

页码：3776 / 3780

页数：5

共 60 条

[1] Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648) [J].

Aiello, Stefania ;

Wells, Geoffrey ;

Stone, Erica L. ;

Kadri, Hachemi ;

Bazzi, Rana ;

Bell, David R. ;

Stevens, Malcolm F. G. ;

Matthews, Charles S. ;

Bradshaw, Tracey D. ;

Westwell, Andrew D. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (16) :5135-5139

[2] Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles [J].

Bahrami, Kiumars ;

Khodaei, M. Mehdi ;

Naali, Fardin .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6835-6837

[3] Synthesis of 1,2-disubstituted benzimidazoles, 2-substituted benzimidazoles and 2-substituted benzothiazoles in SDS micelles [J].

Bahrami, Kiumars ;

Khodaei, Mohammad M. ;

Nejati, Akbar .

GREEN CHEMISTRY, 2010, 12 (07) :1237-1241

[4] In situ oxidation-imine formation-reduction routes from alcohols to amines [J].

Blackburn, L ;

Taylor, RJK .

ORGANIC LETTERS, 2001, 3 (11) :1637-1639

[5] Synthesis of Benzazoles by Hydrogen-Transfer Catalysis [J].

Blacker, A. John ;

Farah, Mohamed M. ;

Hall, Michael I. ;

Marsden, Stephen P. ;

Saidi, Ourida ;

Williams, Jonathan M. J. .

ORGANIC LETTERS, 2009, 11 (09) :2039-2042

[6] Efficient Aerobic Oxidative Synthesis of 2-Substituted Benzoxazoles, Benzothiazoles, and Benzimidazoles Catalyzed by 4-Methoxy-TEMPO [J].

Chen, Yong-Xing ;

Qian, Ling-Feng ;

Zhang, Wei ;

Han, Bing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) :9330-9333

[7] Oxidation of secondary amines catalyzed by dirhodium caprolactamate [J].

Choi, Hojae ;

Doyle, Michael P. .

CHEMICAL COMMUNICATIONS, 2007, (07) :745-747

[8] Convenient and clean synthesis of imines from primary benzylamines [J].

Chu, Guobiao ;

Li, Chunbao .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4716-4719

[9] Synthesis, structure-activity relationships, and antitumor studies of 2-benzoxazolyl hydrazones derived from alpha-(N)-acyl heteroaromatics [J].

Easmon, Johnny ;

Purstinger, Gerhard ;

Thies, Katrin-Sofia ;

Heinisch, Gottfried ;

Hofmann, Johann .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (21) :6343-6350

[10] Gold nanoparticles on hydrotalcites as efficient catalysts for oxidant-free dehydrogenation of alcohols [J].

Fang, Wenhao ;

Zhang, Qinghong ;

Chen, Jing ;

Deng, Weiping ;

Wang, Ye .

CHEMICAL COMMUNICATIONS, 2010, 46 (09) :1547-1549

← 1 2 3 4 5 6 →