Regioselective Synthesis of 1-Cyano-3-arylindolizines: Construction of Pyrroles via DDQ-Mediated Ring Closure of Cyclopropyl Pyridines

被引：3

作者：

Joshi, Dirgha Raj ^{[1
,2
]}

Kim, Ikyon ^{[1
,2
]}

机构：

[1] Yonsei Univ, Coll Pharm, 85 Songdogwahak Ro, Incheon 21983, South Korea

[2] Yonsei Univ, Yonsei Inst Pharmaceut Sci, 85 Songdogwahak Ro, Incheon 21983, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 17期

基金：

新加坡国家研究基金会;

关键词：

Indolizine; Cyclopropanation; Annulation; Domino reaction; Oxidative cyclization; DONOR-ACCEPTOR CYCLOPROPANES; INDOLIZINES; CYCLIZATION; CYCLOADDITION; REARRANGEMENT; DERIVATIVES; ARYLATION; EXPANSION; OXIDATION; IODINE;

D O I：

10.1002/adsc.202200590

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A modular approach to a wide range of 1-cyano-3-(hetero)arylindolizines through aldol-cyclopropanation-oxidative cycloisomerization is described where DDQ was utilized for the regioselective synthesis of the pyrrole units from cyclopropyl pyridines for the first time. A key to success is regioselective oxidation of benzylic position by DDQ, which enabled us to access to one regioisomer out of two possible ones. Homo-dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ has been discovered for the first time as well.

引用

页码：3016 / 3022

页数：7

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