Three-component bis-heterocycliation for synthesis of 2-aminobenzo[4,5]thieno[3,2-d]thiazoles

被引：55

作者：

Huang, Huawen ^{[1
]}

Qu, Zhonghua ^{[1
]}

Ji, Xiaochen ^{[1
]}

Deng, Guo-Jun ^{[1
]}

机构：

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

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 08期

基金：

中国国家自然科学基金;

关键词：

IRON-CATALYZED CYCLIZATION; OXIME ACETATES; KETOXIME CARBOXYLATES; POLYSUBSTITUTED PYRIDINES; TANDEM ANNULATION; FACILE SYNTHESIS; AMINO-HECK; COPPER; THIAZOLE; STRATEGY;

D O I：

10.1039/c8qo01365a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cooperative base system has been developed for the novel three component bis-heterocyclization of methylketoxime acetates. In a reaction complementary to previous thiazole and benzo[4,5]thieno[3,2-d]thiazole formation, the present protocol provides an effective entry to 2-aminobenzo[4,5]thieno[3,2-d]thiazoles. Mechanistically, the formation of trisulfur radical anion [S-3](-) and Willgerodt-Kindler-type sulfuration would be the key for this transformation.

引用

页码：1146 / 1150

页数：5

共 70 条

[1] Redox-Divergent Synthesis of Fluoroalkylated Pyridines and 2-Pyridones through Cu-Catalyzed N-O Cleavage of Oxime Acetates [J].

Bai, Dachang ;

Wang, Xueli ;

Zheng, Guangfan ;

Li, Xingwei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (22) :6633-6637

[2] Beyond Acid Strength in Zeolites: Soft Framework Counteranions for Stabilization of Carbocations on Zeolites and Its Implication in Organic Synthesis [J].

Cabrero-Antonino, Jose R. ;

Leyva-Perez, Antonio ;

Corma, Avelino .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) :5658-5661

[3] Ubiquitous trisulfur radical anion: fundamentals and applications in materials science, electrochemistry, analytical chemistry and geochemistry [J].

Chivers, Tristram ;

Elder, Philip J. W. .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (14) :5996-6005

[4] Multicomponent reactions: advanced tools for sustainable organic synthesis [J].

Cioc, Razvan C. ;

Ruijter, Eelco ;

Orru, Romano V. A. .

GREEN CHEMISTRY, 2014, 16 (06) :2958-2975

[5]

Collins KD, 2014, NAT CHEM, V6, P859, DOI [10.1038/NCHEM.2062, 10.1038/nchem.2062]

[6] Thiazole and Oxazole Alkaloids: Isolation and Synthesis [J].

Davyt, Danilo ;

Serra, Gloria .

MARINE DRUGS, 2010, 8 (11) :2755-2780

[7] Copper-catalyzed arylation of heterocycle C-H bonds [J].

Do, Hien-Quang ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) :12404-+

[8] Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: a facile synthesis of 2-arylpyrroles [J].

Du, Wei ;

Zhao, Mi-Na ;

Ren, Zhi-Hui ;

Wang, Yao-Yu ;

Guan, Zheng-Hui .

CHEMICAL COMMUNICATIONS, 2014, 50 (56) :7437-7439

[9] I2-Triggered Reductive Generation of N-Centered Iminyl Radicals: An Isatin-to-Quinoline Strategy for the Introduction of Primary Amides [J].

Gao, Qinghe ;

Liu, Zhaomin ;

Wang, Yakun ;

Wu, Xia ;

Zhang, Jixia ;

Wu, Anxin .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (07) :1364-1369

[10] Direct synthesis of 2-methylpyridines via I2-triggered [3+2+1] annulation of aryl methyl ketoxime acetates with triethylamine as the carbon source [J].

Gao, Qinghe ;

Yan, Huijuan ;

Wu, Manman ;

Sun, Jiajia ;

Yan, Xiqing ;

Wu, Anxin .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (13) :2342-2348

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