Organocatalytic C3-functionalization of indolizines: synthesis of biologically important indolizine derivatives

被引：24
作者：
Zhang, Yi-Zhu [1 ]
Sheng, Feng-Tao [1 ]
Zhu, Zuoquan [2 ,3 ]
Li, Zhi-Ming [1 ]
Zhang, Shu [2 ,3 ]
Tan, Wei [1 ]
Shi, Feng [1 ]
机构：
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China
[2] Nanjing Med Univ, Affiliated Hosp 1, Dept Radiat Oncol, Nanjing 210029, Peoples R China
[3] Nanjing Med Univ, Affiliated Hosp 1, Dept Radiotherapy, Nanjing 210029, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 29期
基金：
中国国家自然科学基金;
关键词：
ORTHO-QUINONE METHIDES; CHIRAL PHOSPHORIC-ACID; DIELS-ALDER REACTION; BRONSTED ACID; 4+2 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; C3; FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; POTENT INHIBITORS; CATALYSIS;
D O I：
10.1039/d0ob01230k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Bronsted acid-catalyzed C3-alkylation of indolizines has been established with different electrophiles such asortho-hydroxybenzyl alcohols, other precursors ofpara-quinone methides andortho-quinone methides, and 2-indolylmethanol as well. By using this approach, a series of C3-functionalized indolizines were synthesized in overall good yields (up to 89%). These examples demonstrate that the Bronsted acid-catalyzed C3-alkylation of indolizines has a wide applicability, which can serve as a useful method for synthesizing C3-functionalized indolizine derivatives with structural diversity. This reaction has fulfilled the task of developing organocatalytic C3-functionalization of indolizines for the synthesis of biologically important indolizine derivatives.
引用
收藏
页码：5688 / 5696
页数：9
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