Microwave assisted, one-pot four component designing of 1-butyl-4,5-bis(4-chlorophenyl)-2-aryl-1H-imidazoles

A novel series of 1-butyl-4,5-bis(<i>p</i>-chlorophenyl)-2-phenyl-1H-imidazole derivatives <b>5–14</b> were prepared via one-pot cyclo-condensation of aryl aldehyde derivatives, butylamine, 1,2-bis(4-chlorophenyl)-1,2-ethanedione &amp; CH<sub>3</sub>COONH<sub>4</sub>, undergo microwave irradiation employing 4-methylbenzenesulfonic acid (PTSA) as acidic catalyst. Also, the same compounds 1,2,4,5-tetrasubstituted-1H-imidazole products <b>5–14</b> were designed under thermal reaction condition. By optimizing the two-reaction method, it was found that under conventional condition (reflux method), the identical products <b>5–14</b> were generated in good yields (68–87%) in about 10 h. While using the microwave irradiation is an effective and clean technique than the traditional thermal method and gives the same products with higher yields (71–89%) and purity in less time (7–9 min). Additionally, we find that the concentration of <i>p</i>-toluenesulfonic acid affects both the reaction time and the yield. The structures of the prepared components were approved via Infrared spectra, Nuclear Magnetic Resonance and elementals analysis.

Publication Details

Journal
Figshare
Published
2025-01-01
DOI
https://doi.org/10.6084/m9.figshare.28513267
Primary Topic
Solid-state spectroscopy and crystallography
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article
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article

Microwave assisted, one-pot four component designing of 1-butyl-4,5-bis(4-chlorophenyl)-2-aryl-1H-imidazoles

Figshare
Solid-state spectroscopy and crystallography
article

Microwave assisted, one-pot four component designing of 1-butyl-4,5-bis(4-chlorophenyl)-2-aryl-1H-imidazoles

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Abstract

A novel series of 1-butyl-4,5-bis(<i>p</i>-chlorophenyl)-2-phenyl-1H-imidazole derivatives <b>5–14</b> were prepared via one-pot cyclo-condensation of aryl aldehyde derivatives, butylamine, 1,2-bis(4-chlorophenyl)-1,2-ethanedione &amp; CH<sub>3</sub>COONH<sub>4</sub>, undergo microwave irradiation employing 4-methylbenzenesulfonic acid (PTSA) as acidic catalyst. Also, the same compounds 1,2,4,5-tetrasubstituted-1H-imidazole products <b>5–14</b> were designed under thermal reaction condition. By optimizing the two-reaction method, it was found that under conventional condition (reflux method), the identical products <b>5–14</b> were generated in good yields (68–87%) in about 10 h. While using the microwave irradiation is an effective and clean technique than the traditional thermal method and gives the same products with higher yields (71–89%) and purity in less time (7–9 min). Additionally, we find that the concentration of <i>p</i>-toluenesulfonic acid affects both the reaction time and the yield. The structures of the prepared components were approved via Infrared spectra, Nuclear Magnetic Resonance and elementals analysis.

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Microwave assisted, one-pot four component designing of 1-butyl-4,5-bis(4-chlorophenyl)-2-aryl-1H-imidazoles · Figshare (2025) | TGRS Research Map | TGRS