Palladium-catalyzed regioselective synthesis of benzosultams from functionalized ynamides and benzotriazoles/tetrazoles

被引：12

作者：

Reddy, Alla Siva ^{[1
]}

Kumari, A. Leela Siva ^{[1
]}

Swamy, K. C. Kumara ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

TETRAHEDRON | 2017年 / 73卷 / 19期

关键词：

Ynamides; Benzotriazoles; Pd]-catalysis; Cyclization; Benzosultams; BIOLOGICAL-ACTIVITY; DERIVATIVES; ALKENES; SYSTEMS;

D O I：

10.1016/j.tet.2017.03.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed highly regioselective synthesis of benzotriazole appended benzosultams by the tandem-cyclization of functionalized ynamides with benzotriazoles has been accomplished. This transformation involves the formation of both C-N and C-C bonds in a single step. Donor solvents appear to enhance the yields of the products. The methodology is also applicable for the generation of triazole/tetrazole appended benzosultams. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2766 / 2773

页数：8

共 28 条

[1]

[Anonymous], 1997, SHELX 97 PROGRAM CRY

[2] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF BENZOTRIAZOLE DERIVATIVES STRUCTURALLY RELATED TO TRAZODONE [J].

CALIENDO, G ;

DICARLO, R ;

GRECO, G ;

MELI, R ;

NOVELLINO, E ;

PERISSUTTI, E ;

SANTAGADA, V .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (01) :77-84

[3] Gold-Catalyzed Intermolecular [4+2] and [2+2+2] Cycloadditions of Ynamides with Alkenes [J].

Dateer, Ramesh B. ;

Shaibu, Balagopal S. ;

Liu, Rai-Shung .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) :113-117

[4] One-Pot Sonogashira Coupling-Cyclization toward Regioselective Synthesis of Benzosultams [J].

Debnath, Sudarshan ;

Mondal, Shovan .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) :3940-3948

[5] Conventional and microwave assisted synthesis of 2-oxo-4-substituted aryl-azetidine derivatives of benzotriazole: A new class of biological compounds [J].

Dubey, Adesh ;

Srivastava, S. K. ;

Srivastava, S. D. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (01) :569-573

[6] Total synthesis of cyclic heptapeptide Rolloamide B [J].

El Khatib, Mirna ;

Elagawany, Mohamed ;

Caliskan, Eray ;

Davis, Emily Faith ;

Faidallah, Hassan M. ;

El-feky, Said A. ;

Katritzky, Alan R. .

CHEMICAL COMMUNICATIONS, 2013, 49 (26) :2631-2633

[7] Stereoselective Synthesis of Multisubstituted Enamides via Rhodium-Catalyzed Carbozincation of Ynamides [J].

Gourdet, Benoit ;

Lam, Hon Wai .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3802-+

[8] Copper-catalyzed tandem synthesis of [1,2,3]triazolo[5,1-a]isoquinolines and their transformation to 1,3-disubstituted isoquinolines [J].

Hu, Yuan-Yuan ;

Hu, Jie ;

Wang, Xiang-Chuan ;

Guo, Li-Na ;

Shu, Xing-Zhong ;

Niu, Yan-Ning ;

Liang, Yong-Min .

TETRAHEDRON, 2010, 66 (01) :80-86

[9] Sultam Synthesis via Cu-Catalyzed Intermolecular Carboamination of Alkenes with N-Fluorobenzenesulfonimide [J].

Kaneko, Keiichi ;

Yoshino, Tatsuhiko ;

Matsunaga, Shigeki ;

Kanai, Motomu .

ORGANIC LETTERS, 2013, 15 (10) :2502-2505

[10] Synthesis of Heterocycles Mediated by Benzotriazole. 2. Bicyclic Systems [J].

Katritzky, Alan R. ;

Rachwal, Stanislaw .

CHEMICAL REVIEWS, 2011, 111 (11) :7063-7120

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