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

页码：5688 / 5696

页数：9

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