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

Heterocyclic communications

article

Simin Vazirimehr¹  Abolghasem Davoodnia¹  Mahboobeh Nakhaei-Moghaddam²  Niloofar Tavakoli-Hoseini¹ 

[1] Department of Chemistry, Mashhad Branch, Islamic Azad University;Department of Biology, Mashhad Branch, Islamic Azad University;Department of Biochemistry and Clinical Laboratories, Tabriz University of Medical Sciences

关键词: antibacterial;    hexahydroquinoline;    pyrrole;    ultrasonic irradiation;   

DOI  :  10.1515/hc-2016-0164

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

Condensation reaction of dimedone with 2-amino-1-methyl-4,5-diphenyl-1 H -pyrrole-3-carbonitrile in ethanol containing a catalytic amount of p -toluenesulfonic acid (TsOH) afforded 2-(5,5-dimethyl-3-oxocyclohex-1-enylamino)-1-methyl-4,5-diphenyl-1 H -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, 1 H NMR, and 13 C NMR spectra, elemental analysis and evaluated for their antibacterial activity against Gram-positive bacteria ( Staphylococcus aureus and Micrococcus luteus ) and Gram-negative bacterium ( Escherichia coli ).

【 授权许可】

CC BY|CC BY-NC-ND