Iodine Mediated Base-Controlled Regio-Selective Annulation of 2-(Pyridin-2-yl)acetate Derivatives with Acrylic Esters for the Synthesis of Indolizines

被引：13
|
作者：
Fang, Youlai [1 ,2 ]
Li, Fei [1 ,2 ]
Yang, Yuzhu [1 ,2 ]
Liu, Xiaolan [1 ,2 ]
Pan, Weidong [1 ,2 ]
机构：
[1] Guizhou Med Univ, State Key Lab Funct & Applicat Med Plants, 3491 Baijin Rd, Guiyang 550014, Peoples R China
[2] Guizhou Prov & Chinese Acad Sci, Key Lab Chem Nat Prod, 3491 Baijin Rd, Guiyang 550014, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 06期
基金：
中国科学院西部之光基金;
关键词：
iodine; base-controlled; regio-selective; radical process; proto-deiodination; ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; OXIDATIVE CYCLIZATION; FUNCTIONALIZED INDOLIZINES; SUBSTITUTED INDOLIZINES; CATALYZED ANNULATION; PROPARGYL CARBONATES; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; C-C;
D O I：
10.1002/adsc.202000103
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An iodine mediated base-controlled reaction between 2-(pyridin-2-yl)acetate derivatives and acrylic esters has been developed for the selective synthesis of 1,3-disubstituted indolizines and 1,2-disubstituted indolizines. A single-pot reaction of 2-(pyridin-2-yl)acetate derivatives and acrylic esters in the presence of CsOAc delivers 1,3-disubstitued indolizines, while KHCO3 promotes the formation of C3-iodo indolizines, which could be further de-iodinated in the presence of copper powder, affording 1,2-disubstituted indolizines via a sequential stepwise fashion. A plausible reaction mechanism involving radical process has been proposed for this reaction. Pd-catalzyed reaction of C3-iodo indolizines with aryl boronic acids has been described.
引用
收藏
页码：1333 / 1344
页数：12
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