Efficient 2-Aryl Benzothiazole Formation from Aryl Ketones and 2-Aminobenzenethiols under Metal-Free Conditions

被引：92

作者：

Liao, Yunfeng ^{[1
]}

Qi, Hongrui ^{[1
]}

Chen, Shanping ^{[1
]}

Jiang, Pengcheng ^{[1
]}

Zhou, Wang ^{[2
]}

Deng, Guo-Jun ^{[1
]}

机构：

[1] Xiangtan Univ, Coll Chem, Key Lab Environm Friendly Chem & Applicat, Minist Educ, Xiangtan 411105, Peoples R China

[2] Xiangtan Univ, Coll Chem Engn, Xiangtan 411105, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 23期

基金：

中国国家自然科学基金;

关键词：

C-H ARYLATION; ONE-POT SYNTHESIS; INTRAMOLECULAR CYCLIZATION; OXIDATIVE CYCLIZATION; CARBOXYLIC-ACIDS; FACILE SYNTHESIS; BENZOXAZOLES; HETEROARENES; AZOLES; 2-ACYLBENZOTHIAZOLES;

D O I：

10.1021/ol302902e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aryl benzothiazole formation from aryl ketones and 2-aminobenzenethiols under metal- and I-2-free conditions was described. Various 2-aryl benzothiazoles were selectively obtained in good yields using molecular oxygen as oxidant. DMSO played an important role in this transformation. Functional groups such as methyl, methoxy, fluoro, chloro, bromo and nitro groups were tolerated under the optimized reaction conditions.

引用

页码：6004 / 6007

页数：4

共 50 条

[1] Elemental sulfur mediated 2-substituted benzothiazole formation from 2-aminobenzenethiols and arylacetylenes or styrenes under metal-free conditions
Li, Guozheng
Jiang, Jingjing
Zhang, Feng
Xiao, Fuhong
Deng, Guo-Jun
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (47) : 10024 - 10028
[2] Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions
Liao, Yunfeng
Jiang, Pengcheng
Chen, Shanping
Xiao, Fuhong
Deng, Guo-Jun
[J]. RSC ADVANCES, 2013, 3 (40): : 18605 - 18608
[3] Radical Route to 1,4-Benzothiazine Derivatives from 2-Aminobenzenethiols and Ketones under Transition-Metal-Free Conditions
Lin, Ya-mei
Lu, Guo-ping
Wang, Rong-kang
Yi, Wen-bin
[J]. ORGANIC LETTERS, 2016, 18 (24) : 6424 - 6427
[4] Three-component 2-aryl substituted benzothiophene formation under transition-metal free conditions
Jiang, Pengcheng
Che, Xingzong
Liao, Yunfeng
Huang, Huawen
Deng, Guo-Jun
[J]. RSC ADVANCES, 2016, 6 (48) : 41751 - 41754
[5] Difluoroalkylation/1,2-aryl migration of allylic alcohols under transition metal-free conditions
Ge, Danhua
Wang, Xin
Chu, Xue-Qiang
[J]. TETRAHEDRON LETTERS, 2021, 70
[6] Transition metal-free synthesis of 2-aryl quinazolines via alcohol dehydrogenation
Hima, P.
Vageesh, M.
Tomasini, Michele
Poater, Albert
Dey, Raju
[J]. MOLECULAR CATALYSIS, 2023, 542
[7] A Base- and Metal-free Protocol for the Synthesis of 2-Aryl/heteroaryl Thiazolines
Chaudhary, Shweta
Milton, Marilyn D.
Garg, Parul
[J]. CHEMISTRYSELECT, 2017, 2 (02): : 650 - 654
[8] Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones
Yao, Qiuli
Liu, Wenbo
Liu, Peng
Ren, Linjing
Fang, Xuehong
Li, Chao-Jun
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (16) : 2721 - 2724
[9] Synthesis, XRD and Mechanistic Studies of α-Aryl-β,β-ditosyloxy Ketones: An Oxidative 1,2-Aryl Migration in α,β-Unsaturated Diaryl Ketones Under Metal Free Conditions
Kumar, Ravinder
Parkash, Jai
Kamal, Raj
Kumar, Vipan
Saini, Sangeeta
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (01)
[10] Synthesis of 2-aryl and coumarin substituted benzothiazole derivatives
Kenny, Rajesh S.
Mashelkar, Uday C.
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (05) : 1367 - 1369

← 1 2 3 4 5 →