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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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