Ultrasonic synthesis, characterization, and antibacterial evaluation of novel heterocycles containing hexahydroquinoline and pyrrole moieties

• Published in: Heterocyclic communications Vol. 23; no. 1; pp. 65 - 70
• Main Authors: Vazirimehr, Simin, Davoodnia, Abolghasem, Nakhaei-Moghaddam, Mahboobeh, Tavakoli-Hoseini, Niloofar
• Format: Journal Article
• Language: English
• Published: Berlin De Gruyter 01.02.2017; Walter de Gruyter GmbH
• Subjects: Aldehydes; Alkenes; antibacterial; Antiinfectives and antibacterials; Aromatic compounds; Chemical analysis; Coliforms; Cyclic compounds; E coli; Ethanol; Gram-positive bacteria; Heterocyclic compounds; hexahydroquinoline; Hydroxybenzaldehydes; Malononitrile; NMR; Nuclear magnetic resonance; pyrrole; ultrasonic irradiation
• ISSN: 0793-0283; 2191-0197
• DOI: 10.1515/hc-2016-0164

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 ( ).