Synthesis and antimicrobial activity of some methyl‐2‐[ N ‐coumarin‐6′‐yl]‐3‐oxo‐2,3‐dihydro‐1 H ‐isoindolone‐5‐carboxylates
Abstract magnified image N‐substituted furylmethylimines are prepared by condensing 6‐aminocoumarins with furfural, these on sodium borohydride reduction afford N ‐[coumarin‐6′‐yl]‐2‐furylamines. Intramolecular [4+2] cycloaddition of these amines with maleic anhydride results into 3‐[ N ‐coumarin‐6′...
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Published in | Journal of heterocyclic chemistry Vol. 47; no. 1; pp. 214 - 218 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
01.01.2010
|
Online Access | Get full text |
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Summary: | Abstract
magnified image
N‐substituted furylmethylimines are prepared by condensing 6‐aminocoumarins with furfural, these on sodium borohydride reduction afford
N
‐[coumarin‐6′‐yl]‐2‐furylamines. Intramolecular [4+2] cycloaddition of these amines with maleic anhydride results into 3‐[
N
‐coumarin‐6′‐yl]‐4‐oxo‐10‐oxa‐3‐azatricyclo[5.2.1.0
1.5
]dec‐8‐ene‐6‐carboxylic acids
4a
,
4b
,
4c
. The [4+2] cycloadducts on
p
‐toluene sulphonic acid treatment followed by esterification yield the titled compounds. Compound
5a
,
5b
,
5c
was also reduced to isoindolone alcohol
7a
,
7b
,
7c
by sodium borohydride in the presence of a base. All the compounds have been tested
in vitro
for their antimicrobial activity against gram‐positive bacteria
Bacillus subtilis, Staphylococcus aureus
, one gram‐negative bacteria,
Escherichia coli
, and one fungal strain
Candida albicans
at 100 μg/mL concentration. J. Heterocyclic Chem., 2010. |
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ISSN: | 0022-152X 1943-5193 |
DOI: | 10.1002/jhet.274 |