Diastereoselective Synthesis of 1, 10-Dihydropyrrolo[1, 2-a][1, 10]phenanthroline Derivatives via 1, 3-Dipolar Cycloaddition Reaction

doi:10.1007/s40242-013-3224-2

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (6): 1089-1093.doi: 10.1007/s40242-013-3224-2

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Diastereoselective Synthesis of 1, 10-Dihydropyrrolo[1, 2-a][1, 10]phenanthroline Derivatives via 1, 3-Dipolar Cycloaddition Reaction

LIU Zhen-ming¹, FANG Jun², YAN Chao-guo²

1. Analysis and Test Center, Yangzhou 225002, P. R. China;
2. College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. China

Received:2013-05-20 Revised:2013-06-05 Online:2013-12-01 Published:2013-06-24
Contact: YAN Chao-guo E-mail:cgyan@yzu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21172189) and the Priority Academic Program Development of Jiangsu Higher Education Institutions, China.

Abstract

Abstract:

The functionalized 1,10-dihydropyrrolo[1,2-a][1,10]phenanthroline derivatives were synthesized in good yields and with high diastereoselectivity by 1,3-dipolar cycloaddition reactions of N-phenacylphenanthrolinium bromides or N-ethoxycarbonylmethylene phenanthrolinium bromide with various nitrostyrenes in acetonitrile at room temperature in the presence of triethylamine.

Key words: Pyridinium ylide, Phenanthroline, Pyrrolo[1,2-a][1,10]phenanthroline, 1,3-Dipolar cycloaddition, Diastereoselectivity

LIU Zhen-ming, FANG Jun, YAN Chao-guo. Diastereoselective Synthesis of 1, 10-Dihydropyrrolo[1, 2-a][1, 10]phenanthroline Derivatives via 1, 3-Dipolar Cycloaddition Reaction[J]. Chemical Research in Chinese Universities, 2013, 29(6): 1089-1093.

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Diastereoselective Synthesis of 1, 10-Dihydropyrrolo[1, 2-a][1, 10]phenanthroline Derivatives via 1, 3-Dipolar Cycloaddition Reaction

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