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
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
收藏
页码:2766 / 2773
页数:8
相关论文
共 28 条
[21]   Domino Heck-Aza-Michael Reactions: A One-Pot, Sequential Three-Component Approach to 1.1-Dioxido-1,2-benzisothiazoline-3-acetic Acid [J].
Rolfe, Alan ;
Young, Kyle ;
Hanson, Paul R. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) :5254-5262
[22]   Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy [J].
Rolfe, Alan ;
Hanson, Paul R. .
TETRAHEDRON LETTERS, 2009, 50 (50) :6935-6937
[23]   Design, synthesis and evaluation of benzotriazole derivatives as novel antifungal agents [J].
Shah, Jay J. ;
Khedkar, Vijay ;
Coutinho, Evans C. ;
Mohanraj, Krishnapriya .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (17) :3730-3737
[24]  
Sheldrick G., 1996, Siemens Area Detector Absorption Correction Software
[25]  
Sheldrick GM, 1999, SHELXTL NT Crystal Structure Analysis Package, Version 5.10
[26]   Synthesis, biological activity and structural study of new benzotriazole-based protein kinase CK2 inhibitors [J].
Swider, R. ;
Maslyk, M. ;
Zapico, J. M. ;
Coderch, C. ;
Panchuk, R. ;
Skorokhyd, N. ;
Schnitzler, A. ;
Niefind, K. ;
de Pascual-Teresa, B. ;
Ramos, A. .
RSC ADVANCES, 2015, 5 (89) :72482-72494
[27]   Palladium-catalyzed synthesis of 2-aminoindoles by a heteroanulation reaction [J].
Witulski, B ;
Alayrac, C ;
Tevzadze-Saeftel, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4257-4260
[28]   Copper sulfate-pentahydrate-1,10-phenanthroline catalyzed amidations of alkynyl bromides. Synthesis of heteroaromatic amine substituted ynamides [J].
Zhang, YS ;
Hsung, RP ;
Tracey, MR ;
Kurtz, KCM ;
Vera, EL .
ORGANIC LETTERS, 2004, 6 (07) :1151-1154