Michael addition of α-azido ketones on iminocoumarin derivatives: an efficient access to new functionalized azido chromenes

被引：16

作者：

Babu, Thelagathoti Hari ^{[1
]}

Kamalraja, Jayabal ^{[1
]}

Muralidharan, Doraiswamy ^{[1
]}

Perumal, Paramasivan T. ^{[1
]}

机构：

[1] Cent Leather Res Inst CSIR, Div Organ Chem, Madras 600020, Tamil Nadu, India

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 32期

关键词：

Michael addition; alpha-Azido ketones; Azido chromenes; Triazolyl chromenes; AZA-WITTIG REACTION; ONE-POT SYNTHESIS; HETEROCYCLIC SYNTHESIS; STAUDINGER REACTION; TERMINAL ALKYNES; AZIDOKETONES; REDUCTION; PYRROLES; ROUTE;

D O I：

10.1016/j.tetlet.2011.05.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

A facile one-pot synthesis of functionalized azido chromenes was achieved by Michael addition of alpha-azido ketones on iminocoumarin derivatives obtained from salicylaldehydes and malononitrile. Synthesized azido chromenes were successfully transformed into triazolyl chromenes by the [3+2] cycloaddition reaction. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4093 / 4096

页数：4

共 34 条

[1]

A facile one-pot synthesis of N-substituted tetrahydroquinolines [J].

Babu, Thelagathoti Hari ;

Shanthi, Gnanamani ;

Perumal, Paramasivan T. .

TETRAHEDRON LETTERS, 2009, 50 (24) :2881-2884

[2]

SYNTHESIS OF REACTIVITY OF LAMBDA-5-PHOSPHAZENES - USES AS SYNTHETIC INTERMEDIATES [J].

BARLUENGA, J ;

PALACIOS, F .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (01) :1-65

[3]

SYNTHESIS OF BETA-FLUOROAZIDES - A ROUTE TO PRIMARY BETA-FLUORO AMINES [J].

BENAISSA, T ;

HAMMAN, S ;

BEGUIN, CG .

JOURNAL OF FLUORINE CHEMISTRY, 1988, 38 (02) :163-173

[4]

Stereoselective acylations of 1,2-azidoalcohols with vinyl acetate, catalyzed by lipase Amano PS [J].

Brenelli, ECS ;

Fernandes, JLN .

TETRAHEDRON-ASYMMETRY, 2003, 14 (10) :1255-1259

[5]

Cordell G. A., 2000, ALKALOIDS CHEM BIOL, V54

[6]

THE AZA-WITTIG REACTION IN HETEROCYCLIC SYNTHESIS - A REVIEW [J].

EGUCHI, S ;

MATSUSHITA, Y ;

YAMASHITA, K .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1992, 24 (02) :209-&

[7]

ELLIS GP, 1977, CHEM HETEROCYCLIC CO, P11

[8]

Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].

Evano, Gwilherm ;

Blanchard, Nicolas ;

Toumi, Mathieu .

CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131

[9]

Domino "Staudinger/semi-aza-Wittig/fragmentation" reactions of γ-azido-β-hydroxyketones [J].

Freifeld, Ilia ;

Shojaei, Heydar ;

Dede, Ruediger ;

Langer, Peter .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6165-6170

[10]

Synthesis of 2-alkylidenepyrrolidines and pyrroles by condensation of 1,3-dicarbonyl dianions with α-azidoketones and subsequent intramolecular Staudinger-aza-Wittig reaction [J].

Freifeld, Ilia ;

Shojaei, Heydar ;

Langer, Peter .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :4965-4968

← 1 2 3 4 →