An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents

Molecules

Hassan M. Faidallah¹  Khalid M. A. Al-Shaikh¹  Tariq R. Sobahi¹  Khalid A. Khan¹ 

[1] Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia; E-Mails:

关键词: dihydrophenanthrene;    X-ray crystallography;    dihydrobenzo[h]quinoline-3-carbonitrile;    antimicrobial activity;   

DOI  :  10.3390/molecules181215704

来源: mdpi

【 摘 要 】

An efficient and novel method for the synthesis in moderate to good yield (72%–84%) of a series of 3-amino-1-substituted-9,10-dihydrophenanthrene-2,4-dicarbonitriles 1–5 via one-pot multi-component reactions of aldehydes, malononitrile, 1-tetralone and ammonium acetate has been delineated. Cyclocondensation attempts of aminocyanophenanthrene derivatives 1, 2, 4 and 5 with acetic anhydride in the presence of conc. H₂SO₄ failed and instead the diacetylamino derivatives 10–13 were obtained. All prepared compounds were structurally elucidated by various spectroscopic methods and X-ray crystallography. N,N-diacetylamino-derivatives of phenanthrene have shown good antimicrobial activity.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.