β-CD/CuI catalyzed regioselective synthesis of iodo substituted 1,2,3-triazoles, imidazo[1,2-a]-pyridines and benzoimidazo[2,1-b] thiazoles in water and their functionalization

被引：32
|
作者：
Dheer, Divya [1 ,2 ]
Rawal, Ravindra K. [3 ]
Singh, Virender [4 ]
Sangwan, P. L. [1 ]
Das, Parthasarathi [1 ]
Shankar, Ravi [1 ,2 ]
机构：
[1] Indian Inst Integrat Med CSIR, Bioorgan Chem Div, Jammu 180001, India
[2] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India
[3] ISFCP, Dept Pharmaceut Chem, Moga 142002, India
[4] NIT, Dept Chem, Jalandhar 144011, Punjab, India
来源：
TETRAHEDRON | 2017年 / 73卷 / 30期
关键词：
beta-Cyclodextrin; lodo-imidazo[1,2-a]pyridines; lodo-triazoles; lodo-benzoimidazo[2,1-b]thiazoles; H AMINATION SYNTHESIS; CYCLIC ADP-RIBOSE; CLICK CHEMISTRY; EFFICIENT SYNTHESIS; ORGANIC AZIDES; ANALOGS; CYCLODEXTRIN; DERIVATIVES; CYCLIZATION; ALKYNE;
D O I：
10.1016/j.tet.2017.05.081
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An environment benign process has been developed for the regioselective synthesis of 5-iodo-1,4-disubstituted-1,2,3-triazoles catalyzed by Cul/beta-CD in water. Moreover, the process was manifested for the efficient synthesis of 2-iodo-imidazo[1,2-a]pyridines and 2-iodo-benzoimidazo[2,1-b]thiazoles in aqueous medium. Additionally, the iodinated derivatives were successfully modified via palladium catalyzed coupling reactions. The salient features of this methodology are in-situ formation of 1-iodoalkyne & alkyl/aryl azide under mild reaction conditions, high regio-selectivity and use of water as a greener solvent. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4295 / 4306
页数：12
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