Formal [4+1] cycloaddition strategy for the synthesis of dihydrobenzofurans via Michael addition of 2-(2-nitrovinyl)-phenols and malonate esters (C1 synthon) and subsequent iodine-catalyzed oxidative annulation

被引：7
|
作者：
Leng, Jiaying [1 ]
Meng, Jiang [1 ]
Luo, Xiaoyan [1 ]
Deng, Wei-Ping [1 ]
机构：
[1] East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab New Drug Design, Shanghai 200237, Peoples R China
来源：
TETRAHEDRON | 2018年 / 74卷 / 49期
基金：
上海市自然科学基金;
关键词：
Iodine-catalyzed; Dihydrobenzofurans; Nitroalkenes; Malonate esters; AZOMETHINE YLIDES; BOND FORMATION; CONSTRUCTION; 2,3-DIHYDROBENZOFURANS; AMINATION; CYCLIZATION; INHIBITORS; ALLENES; CELLS; ACID;
D O I：
10.1016/j.tet.2018.09.028
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel [4 +1] cycloaddition protocol for the synthesis of dihydrobenzo(naphtho)furan skeletons from readily available 2-(2-nitrovinyl)-phen(naphth)ols and malonate esters via a tandem Michael addition/iodine-catalyzed oxidative annulation has been developed. This method provides a new and facile application of malonate esters as 1,1-nucleophilicielectrophilic type C1 synthons without a pre-functionalization step and the plausible reaction mechanism is proposed. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6993 / 6999
页数：7
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