Ultrasonic synthesis, characterization, and antibacterial evaluation of novel heterocycles containing hexahydroquinoline and pyrrole moieties
Condensation reaction of dimedone with 2-amino-1-methyl-4,5-diphenyl-1 -pyrrole-3-carbonitrile in ethanol containing a catalytic amount of -toluenesulfonic acid (TsOH) afforded 2-(5,5-dimethyl-3-oxocyclohex-1-enylamino)-1-methyl-4,5-diphenyl-1 -pyrrole-3-carbonitrile. This compound was then treated...
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Published in | Heterocyclic communications Vol. 23; no. 1; pp. 65 - 70 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Berlin
De Gruyter
01.02.2017
Walter de Gruyter GmbH |
Subjects | |
Online Access | Get full text |
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Summary: | Condensation reaction of dimedone with 2-amino-1-methyl-4,5-diphenyl-1
-pyrrole-3-carbonitrile in ethanol containing a catalytic amount of
-toluenesulfonic acid (TsOH) afforded 2-(5,5-dimethyl-3-oxocyclohex-1-enylamino)-1-methyl-4,5-diphenyl-1
-pyrrole-3-carbonitrile. This compound was then treated with olefins, formed by Knoevenagel condensation of aryl aldehydes and malononitrile, in ethanol in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as catalyst to give novel cyclic compounds in high yields. A new hexacyclic heterocyclic compound was formed when 2-hydroxybenzaldehyde was used as the aldehyde. The reactions were done using ultrasonic irradiation. The synthesized compounds were characterized by IR,
H NMR, and
C NMR spectra, elemental analysis and evaluated for their antibacterial activity against Gram-positive bacteria (
and
) and Gram-negative bacterium (
). |
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ISSN: | 0793-0283 2191-0197 |
DOI: | 10.1515/hc-2016-0164 |