Iodine-catalyzed formation of aza-dienes: a novel synthesis of angularly fused hexahydropyrano- and furo[3,2-c]quinoline derivatives

被引：18

作者：

Reddy, B. V. Subba ^{[1
]}

Grewal, Harish ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 07期

关键词：

Molecular iodine; Imino-Diels-Alder reaction; Angularly fused quinoline derivatives; ONE-POT SYNTHESIS; DIELS-ALDER REACTIONS; MOLECULAR-IODINE; VINYL ETHERS; TRIMETHYLSILYL CYANIDE; EFFICIENT SYNTHESIS; FACILE SYNTHESIS; ENOL ETHERS; 1,2,3,4-TETRAHYDROQUINOLINES; ACTIVATION;

D O I：

10.1016/j.tetlet.2010.12.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In situ generated aza-diene, from NAmethyl-N-(trimethylsilyl)methyl]aniline in the presence of a catalytic amount of molecular iodine undergoes smooth [4+2] cycloaddition with electron-rich enol ethers, such as 3,4-dihydro-2H-pyran and 2,3-dihydrofuran under mild and neutral conditions to afford the corresponding hexahydropyrano- and furo[3,2-c]quinoline derivatives, respectively, in good yields with cis-selectivity. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：761 / 763

页数：3

共 48 条

[1] An Efficient Method for the Synthesis of Indolo[3,2-c]quinoline Derivatives Catalyzed by Iodine
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[7] NITRILES IN HETEROCYCLIC SYNTHESIS - NOVEL SYNTHESIS OF BENZO[C]-COUMARIN AND OF BENZO[C]PYRANO[3,2-C]QUINOLINE DERIVATIVES
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[10] Radical Cation Salts Induced aza-Diels-Alder Reaction: Synthesis of Hexahydrofuro[3,2-c]-quinoline Derivatives
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