Synthesis of novel coumarin and benzocoumarin ...

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Title Synthesis of novel coumarin and benzocoumarin derivatives and their biological and photophysical studies.
Author(s) A. Abd-El-Aziz, H. Mohamed, S. Mohammed, S. Zahid, A. Ata, A. Bedair, A. El-Agrody, P. Harvey
Journal Section Title: Heterocyclic Compounds (One Hetero Atom), Journal of Heterocyclic Chemistry
Date 2007
Volume 44
Issue 6
Start page 1287
End page 1301
Abstract Several derivs. of coumarin-3N-carboxamides have been prepd. via the reaction of the coumarin-3-carbonyl chloride with a no. of nucleophiles. Novel double-headed coumarin-3N-carboxamides were also produced using the same method. The Pechmann-Duisberg reaction was applied to prep. new benzo[f]- benzo[h]coumarins and 4-(chloromethyl)-pyrano[3,2-c]coumarin-2-one. The reaction of 1-chloromethylbenzo[f]coumarins with cyanide anion under different reaction conditions was also investigated in order to assess its suitability for nucleophilic substitution reactions as well as ring transformation products. Synthesis of 1-((benzo[d]thiazol-2-yl)methyl)-9-hydroxybenzo[f]coumarin represented the first example of methylene bridge-head heterocycle-contg. benzo[f]coumarin. Some of the newly prepd. coumarins exhibited anti-bacterial activity against Gram Pos. and Gram neg. bacteria. Compd. I was found to be active against all the screened bacteria. Photophys. studies were performed on selected fluorescent benzo[f]- and benzo[h]coumarins and the quantum yields were also calcd. All new compds. were characterized by IR, MS, 1H and 13C NMR, as well as elemental anal. [on SciFinder(R)]
DOI 10.1002/jhet.5570440610
ISSN 0022-152X

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