An efficient approach to the synthesis of highly congested 9,10-dihydrophenanthrene-2,4-dicarbonitriles and their biological evaluation as antimicrobial agents

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Hassan M FaidallahAbdullah M Asiri

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 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.

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Nov 8, 2011·Acta Crystallographica. Section E, Structure Reports Online·Abdullah M AsiriEdward R T Tiekink
Jan 6, 2012·Acta Crystallographica. Section E, Structure Reports Online·Abdullah M AsiriSeik Weng Ng
Jan 6, 2012·Acta Crystallographica. Section E, Structure Reports Online·Abdullah M AsiriSeik Weng Ng
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May 19, 2012·Acta Crystallographica. Section E, Structure Reports Online·Abdullah M AsiriEdward R T Tiekink

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Citations

Apr 23, 2017·Bioorganic & Medicinal Chemistry Letters·Niggula Praveen KumarNagula Shankaraiah

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Methods Mentioned

BETA
X-ray
column chromatography

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