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Molecules 2013, 18(12), 15704-15716; doi:10.3390/molecules181215704
Article

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

1,* , 1
,
1
,
1
 and
1,2
1 Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia 2 Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 8 August 2013 / Revised: 20 November 2013 / Accepted: 10 December 2013 / Published: 16 December 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

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 15 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 1013 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.
Keywords: dihydrophenanthrene; X-ray crystallography; dihydrobenzo[h]quinoline-3-carbonitrile; antimicrobial activity dihydrophenanthrene; X-ray crystallography; dihydrobenzo[h]quinoline-3-carbonitrile; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Faidallah, H.M.; Al-Shaikh, K.M.A.; Sobahi, T.R.; Khan, K.A.; Asiri, A.M. An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents. Molecules 2013, 18, 15704-15716.

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