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

Received: 8 August 2013; in revised form: 20 November 2013 / Accepted: 10 December 2013 / Published: 16 December 2013
(This article belongs to the Section Organic Synthesis)
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.
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
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MDPI and ACS Style

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.

AMA Style

Faidallah HM, Al-Shaikh KMA, Sobahi TR, Khan KA, Asiri AM. 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(12):15704-15716.

Chicago/Turabian Style

Faidallah, Hassan M.; Al-Shaikh, Khalid M.A.; Sobahi, Tariq R.; Khan, Khalid A.; Asiri, Abdullah M. 2013. "An Efficient Approach to the Synthesis of Highly Congested 9,10-Dihydrophenanthrene-2,4-dicarbonitriles and Their Biological Evaluation as Antimicrobial Agents." Molecules 18, no. 12: 15704-15716.

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