Peroxides as "Switches" of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates

被引：68

作者：

Chen, Xiao-Lan ^{[1
]}

Li, Xu ^{[1
]}

Qu, Ling-Bo ^{[1
,2
]}

Tang, Yu-Chun ^{[1
]}

Mai, Wen-Peng ^{[2
]}

Wei, Dong-Hui ^{[1
]}

Bi, Wen-Zhu ^{[1
]}

Duan, Li-Kun ^{[1
]}

Sun, Kai ^{[1
]}

Chen, Jian-Yu ^{[1
]}

Ke, Dian-Dian ^{[1
]}

Zhao, Yu-Fen ^{[1
,3
]}

机构：

[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Henan Province, Peoples R China

[2] Henan Univ Technol, Chem & Chem Engn Sch, Zhengzhou 450052, Henan Province, Peoples R China

[3] Xiamen Univ, Dept Chem, Xiamen 361005, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 17期

基金：

中国国家自然科学基金;

关键词：

BIOLOGICAL EVALUATION; INHIBITORS; DESIGN; DERIVATIVES; ARYL; BENZOTHIAZOLES; TRANSFORMYLASE; ALKYNES; ACID;

D O I：

10.1021/jo501791n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two mild and metal-free methods for the preparation of two kinds of important benzothiazole derivatives, 2-acylbenzothiazoles and dialkyl benzothiazol-2-ylphosphonates, respectively, were developed. The diallcyl H-phosphonate (RO)(2)P(O)H exists in equilibrium with its tautomer dialkyl phosphite (RO)(2)POH. TBHP triggered alpha-carbon-centered phosphite radical formation, whereas DTBP triggered phosphorus-centered phosphonate radical formation. The two types of radicals led respectively to two different reaction processes, the direct C-2-acylation of benzothiazoles and C-2-phosphonation of benzothiazoles.

引用

页码：8407 / 8416

页数：10

共 43 条

[1] Air-stable PinP(O)H as preligand for palladium-catalyzed Kumada couplings of unactivated tosylates [J].

Ackermann, Lutz ;

Althammer, Andreas .

ORGANIC LETTERS, 2006, 8 (16) :3457-3460

[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] THE MICHAELIS-ARBUZOV REARRANGEMENT [J].

BHATTACHARYA, AK ;

THYAGARAJAN, G .

CHEMICAL REVIEWS, 1981, 81 (04) :415-430

[4] Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles [J].

Cressier, Damien ;

Prouillac, Caroline ;

Hernandez, Pierre ;

Amourette, Christine ;

Diserbo, Michel ;

Lion, Claude ;

Rima, Ghassoub .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (14) :5275-5284

[5] Asymmetric synthesis of inhibitors of glycinamide ribonucleotide transformylase [J].

DeMartino, Jessica K. ;

Hwang, Inkyu ;

Connelly, Stephen ;

Wilson, Ian A. ;

Boger, Dale L. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (17) :5441-5448

[6] Pd(II)-Catalyzed Phosphorylation of Aryl C-H Bonds [J].

Feng, Chen-Guo ;

Ye, Mengchun ;

Xiao, Kai-Jiong ;

Li, Suhua ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) :9322-9325

[7] Design and Synthesis of 2-Acylbenzothiazoles via In Situ Cross-Trapping Strategy from Benzothiazoles with Aryl Ketones [J].

Gao, Qinghe ;

Wu, Xia ;

Jia, Fengcheng ;

Liu, Meicai ;

Zhu, Yanping ;

Cai, Qun ;

Wu, Anxin .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (06) :2792-2797

[8] Copper-Catalyzed Aerobic Oxidative Coupling of Terminal Alkynes with H-Phosphonates Leading to Alkynylphosphonates [J].

Gao, Yuxing ;

Wang, Gang ;

Chen, Lu ;

Xu, Pengxiang ;

Zhao, Yufen ;

Zhou, Yongbo ;

Han, Li-Biao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (23) :7956-+

[9] NUCLEOSIDE H-PHOSPHONATES .8. ACTIVATION OF HYDROGEN PHOSPHONATE MONOESTERS BY CHLOROPHOSPHATES AND ARENESULFONYL DERIVATIVES [J].

GAREGG, PJ ;

STAWINSKI, J ;

STROMBERG, R .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :284-287

[10]

Giorgio C, 2003, TETRAHEDRON, V59, P9471

← 1 2 3 4 5 →