A strategic approach to the synthesis of novel class of dispiroheterocyclic derivatives through 1,3 dipolar cycloaddition of azomethine ylide with (E)-3-arylidene-2,3-dihydro-8-nitro-4-quinolone

被引：29

作者：

Chandraprakash, Kumarasamy ^{[1
]}

Sankaran, Mathan ^{[1
]}

Uvarani, Chokalingam ^{[1
]}

Shankar, Ramasamy ^{[2
]}

Ata, Athar ^{[3
]}

Dallemer, Frederic ^{[4
]}

Mohan, Palathurai Subramaniam ^{[1
]}

机构：

[1] Bharathiar Univ, Dept Chem, Sch Chem Sci, Coimbatore 641046, Tamil Nadu, India

[2] Bharathiar Univ, DRDO BU CLS, Coimbatore 641046, Tamil Nadu, India

[3] Univ Winnipeg, Dept Chem, Richardson Coll Environm Sci Complex, Winnipeg, MB R3B2G3, Canada

[4] Univ Aix Marseille I II & III, Lab Chim Provence, CNRS, UMR 6264, F-13397 Marseille 20, France

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 29期

关键词：

1,3 dipolar cycloaddition; Azomethine ylides; (E)-3-Arylidene-2; 3-Dihydro-8-nitro-4-quinolone; Dispiroheterocycles; DENSITY-FUNCTIONAL THEORY; DIELS-ALDER REACTION; BAYLIS-HILLMAN ADDUCTS; GAMMA-LACTAM ANALOG; STEREOSELECTIVE-SYNTHESIS; ANTICONVULSANT ACTIVITY; ANTITUMOR AGENTS; SPIRO-OXINDOLES; INHIBITORS; DISCOVERY;

D O I：

10.1016/j.tetlet.2013.05.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel dispiroheterocyclic system containing 4-quinolone nucleus are prepared by 1,3 dipolar cycloaddition of azomethine ylides with a newly prepared (E)-3-arylidene-2,3-dihydro-8-nitro-4-quinolone as dipolarophile. The ylide was generated in situ from isatin and sarcosine/1,3-thiazolane-4-carboxylic acid. The regio and stereochemistry of the synthesized product was established by H-1, C-13, 2D NMR techniques and single crystal X-ray analysis. The molecular mechanism of this cycloaddition has been investigated by means of the density functional theory (DFT) method. The experimental results of regioselectivity product of 1,3 dipolar cycloaddition have shown good agreement with the computed Frontier molecular orbital calculation (FMO) and fukui function analysis. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3896 / 3901

页数：6

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