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
收藏
页码：379 / 392
页数：14
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