Synthesis of Multisubstituted Pyrroles from Enolizable Aldehydes and Primary Amines Promoted by Iodine

被引：23

作者：

Huang, Wenbo ^{[1
]}

Chen, Shaomin ^{[1
]}

Chen, Zhiyan ^{[1
]}

Yue, Meie ^{[2
]}

Li, Minghao ^{[1
]}

Gu, Yanlong ^{[1
,3
]}

机构：

[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Key Lab Mat Chem Energy Convers & Storage, Hubei Key Lab Mat Chem & Serv Failure,Ministry Ed, Wuhan 430074, Hubei, Peoples R China

[2] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, Qingdao 266042, Shandong, Peoples R China

[3] Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 09期

基金：

中国国家自然科学基金;

关键词：

ONE-POT; SUBSTITUTED PYRROLES; ALDOL CONDENSATION;

D O I：

10.1021/acs.joc.9b00596

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2,4-Trisubstituted pyrroles were synthesized from enolizable aliphatic aldehydes and primary aliphatic amines by using iodine as the dual Lewis acid/mild oxidant. In the presence of 3.0 equiv of TBHP, enolizable alpha,beta-unsaturated aldehyde, for example, cocal reacted with aromatic primary amines to form C2-iodized N-arylpyrroles. An acetal-containing pyrrole was successfully prepared from 4-amino-butyraldehyde diethyl acetal, which can be converted easily to 5,6,7,8-tetrahydroindolizine derivatives.

引用

页码：5655 / 5666

页数：12

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