Stereoselective Synthesis and Antioxidant Activity of Azabicycloadducts Derived from 9,10-Phenanthrenequinone

被引：12

作者：

Arora, Komal ^{[1
]}

Jose, D. ^{[1
]}

Singh, D. ^{[2
]}

Gupta, R. S. ^{[2
]}

Pardasani, P. ^{[1
]}

Pardasani, R. T. ^{[1
]}

机构：

[1] Univ Rajasthan, Dept Chem, Jaipur 302055, Rajasthan, India

[2] Univ Rajasthan, Dept Zool, Jaipur 302055, Rajasthan, India

来源：

HETEROATOM CHEMISTRY | 2009年 / 20卷 / 07期

关键词：

ALPHA-AMINO-ACIDS; AZOMETHINE YLIDES; CARBON-TETRACHLORIDE; 1,3-DIPOLAR CYCLOADDITION; POTENTIAL 1,3-DIPOLES; MACROPHAGE FUNCTION; THIOPROLINE; HEPATOTOXICITY; PYRROLIDINES; MECHANISM;

D O I：

10.1002/hc.20562

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile synthesis of sprio{1-azabicyclo-[3,3,0]-6-octene-8, 1'-phenanthrene}-2'-ones has been accomplished by [3 + 2] cycloaddition of azomethine ylide (amy) generated from 9,10-phenanthrenequinone and different secondary cyclic amino acids, namely, thiazolidine-4-carboxylic acid, L-pyrrolidine-2-carboxylic acid (L-proline), and piperidine-2-carboxylic acid (pipecolinic acid) with electron-deficient dipolarophiles in 67%-79% yield. AM] calculations have been performed to understand the stereochemical course of the cycloaddition. The products have been characterized by elemental analyses and spectroscopic techniques, namely IR, H-1 NMR, and C-13 NMR spectroscopies as well as mass spectrometry. Some of the synthesized cycloadducts showed moderate antioxidant activity. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 20:379-392, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20562

引用

页码：379 / 392

页数：14

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