N-Iodosuccinimide involved one-pot metal-free synthesis of 2-heteroaromatic benzothiazole compounds

被引：17

作者：

Chu, Xianglong ^{[1
]}

Duan, Tiantian ^{[1
]}

Liu, Xuan ^{[1
]}

Feng, Lei ^{[1
]}

Jia, Jiong ^{[1
]}

Ma, Chen ^{[1
,2
,3
]}

机构：

[1] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China

[2] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China

[3] Peking Union Med Coll, Beijing 100050, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 07期

基金：

美国国家科学基金会;

关键词：

DECARBOXYLATIVE ARYLATION; CATALYZED ARYLATION; PARALLEL SYNTHESIS; COPPER; BENZIMIDAZOLES; BENZOXAZOLES; CYCLIZATION; BONDS; ACID;

D O I：

10.1039/c6ob02731h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot protocol for the synthesis of structurally diverse 2-hetarylbenzothiazoles via oxidative condensation of the sp(3) C-H bond with benzothiazoles has been described. This process is metal free and operationally simple. A series of 2-hetarylbenzothiazoles were prepared in moderate to good yield under mild conditions.

引用

页码：1606 / 1611

页数：6

共 32 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] SYNTHESIS OF ORTHO-AMINOTHIOPHENOLS [J].

CHEDEKEL, MR ;

SHARP, DE ;

JEFFERY, GA .

SYNTHETIC COMMUNICATIONS, 1980, 10 (03) :167-173

[3] Base-Promoted Cross-Dehydrogenative Coupling of Quinoline N-Oxides with 1,3-Azoles [J].

Chen, Xiaopei ;

Cui, Xiuling ;

Yang, Fangfang ;

Wu, Yangjie .

ORGANIC LETTERS, 2015, 17 (06) :1445-1448

[4] Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides [J].

Evindar, G ;

Batey, RA .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :1802-1808

[5] KI-catalyzed arylation of benzothiazoles from the coupling of aryl aldehydes with benzothiazoles in neat water [J].

Gao, Yuyu ;

Song, Qiuling ;

Cheng, Guolin ;

Cui, Xiuling .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (07) :1044-1047

[6] Liberation of Copper from Amyloid Plaques: Making a Risk Factor Useful for Alzheimer's Disease Treatment [J].

Geng, Jie ;

Li, Meng ;

Wu, Li ;

Ren, Jinsong ;

Qu, Xiaogang .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (21) :9146-9155

[7] THE USE OF POLYPHOSPHORIC ACID IN THE SYNTHESIS OF 2-ARYL-SUBSTITUTED AND 2-ALKYL-SUBSTITUTED BENZIMIDAZOLES, BENZOXAZOLES AND BENZOTHIAZOLES [J].

HEIN, DW ;

ALHEIM, RJ ;

LEAVITT, JJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (02) :427-429

[8] A Highly Efficient Palladium/Copper Cocatalytic System for Direct Arylation of Heteroarenes: An Unexpected Effect of Cu(Xantphos)I [J].

Huang, Jinkun ;

Chan, Johann ;

Chen, Ying ;

Borths, Christopher J. ;

Baucom, Kyle D. ;

Larsen, Robert D. ;

Faul, Margaret M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3674-+

[9]

Kim YH, 2005, B KOREAN CHEM SOC, V26, P47

[10] Efficient 2-Aryl Benzothiazole Formation from Aryl Ketones and 2-Aminobenzenethiols under Metal-Free Conditions [J].

Liao, Yunfeng ;

Qi, Hongrui ;

Chen, Shanping ;

Jiang, Pengcheng ;

Zhou, Wang ;

Deng, Guo-Jun .

ORGANIC LETTERS, 2012, 14 (23) :6004-6007

← 1 2 3 4 →