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
收藏
页码：3016 / 3022
页数：7
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