Synthesis of 1-(2-bromo-1-arylethyl)-1H-benzotriazoles via NBS promoted addition of 1H-benzotriazole to alkene: Relevance in benzotriazole ring cleavage

被引：4
|
作者：
Singh, Mala [1 ]
Bose, Priyanka [1 ]
Singh, Anoop S. [1 ]
Tiwari, Vinod K. [1 ]
机构：
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
来源：
TETRAHEDRON | 2020年 / 76卷 / 14期
关键词：
N-acyl benzotriazole; 1H-benzotriazole; Benzotriazole ring cleavage (BtRC); N-bromosuccinimide; E-2-ellimination; Ring opening; N-ACYLBENZOTRIAZOLES; ANTIFUNGAL ACTIVITY; BOND FORMATION; BENZOTHIAZOLES; FACILE; PROTOCOL; RADICALS; AMIDES;
D O I：
10.1016/j.tet.2020.131078
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A cost-effective and expeditious one-pot synthesis of 1-(2-bromo-1-arylethyl)-1H-benzotriazoles has been devised by reacting styrene and their derivatives with 1H-benzotriazole in presence of N-bromo-succinimide in anhydrous CH(2)Cl(2 )at room temperature. Further, the resulted compounds undergo E-2-ellimination to afford the respective 1-(1-aryl-vinyl)-1H-benzotriazoles. At the end, 1-(1-phenylvinyl)-1H-benzotriazoles underwent benzotriazole ring cleavage (BtRC) under free radical condition to produce phenanthridine as the final product. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：6
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