Acid-Catalyzed Synthesis of Diverse Indol-3-Yl-Substituted Tetrahydropyridines through Three-Component Reactions

被引：3

作者：

Zhu, Hongmei ^{[1
]}

Chen, Lei ^{[1
]}

Bai, Rongxian ^{[1
]}

Gu, Yanlong ^{[1
,2
,3
]}

机构：

[1] Huazhong Univ Sci & Technol, Key Lab Mat Chem Energy Convers & Storage, Hubei Key Lab Mat Chem & Serv Failure, Minist Educ,Sch Chem & Chem Engn, 1037 Luoyu Rd, Wuhan 430074, Peoples R China

[2] Shihezi Univ, Sch Chem & Chem Engn, Shihezi 832003, Xinjiang, Peoples R China

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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 16期

基金：

中国国家自然科学基金;

关键词：

Acid catalysis; Tetrahydropyridine; Three-component reaction; Indoles; C-H ACTIVATION; MULTICOMPONENT REACTIONS; RU; 24969; INDOLE; AGONIST; DOPAMINE-D-2; GENERATION; ROXINDOLE;

D O I：

10.1002/adsc.202200394

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Two classes of indole-tetrahydropyridine hybrid molecules were synthesized via three-component reactions of: (i) 1-amino-3,3-diethoxypropane, diethyl acetylenedicarboxylate and indole; and (ii) ethyl 3-aminocrotonate, acrolein and 2-methylindoles. These one-pot reactions provided straightforward ways to access indole-tetrahydropyridine hybrid molecules with enriched molecular diversity. The reactions were most likely triggered by Michael addition, and the generated adducts were trapped by the indole component, leading to the formation of indol-3-ylimine intermediate. The obtained indol-3-yl-substituted tetrahydropyridines could be converted into indole-pyridine hybrid molecules with the aid of DDQ.

引用

页码：2883 / 2888

页数：6

共 40 条

[1]

Bartoszyk GD, 1996, J PHARMACOL EXP THER, V276, P41

[2] Multicomponent and One-pot Syntheses of Quinoxalines [J].