Tuesday, 14 June 2016

An expeditious green route toward 2-aryl-4-phenyl-1H-imidazoles

Scheme 1
Ultrasound-assisted synthesis of 2-aryl-4-phenyl-1 H -imidazoles.

A rapid and simple synthetic procedure to synthesize diversely substituted 2-aryl-4-phenyl-1H-imidazoles has been reported. Other salient features of this protocol include milder conditions, atom-economy, easy extraction, and minimum wastes. The present procedure may find application in the synthesis of biologically active molecules.


An expeditious green route toward 2-aryl-4-phenyl-1H-imidazoles

  • Debasish BandyopadhyayEmail author,
  • Lauren C Smith,
  • Daniel R Garcia,
  • Ram N Yadav and
  • Bimal K BanikEmail author
Organic and Medicinal Chemistry Letters20144:9
DOI: 10.1186/s13588-014-0009-7


General procedure for the synthesis of 2-aryl-4-phenyl-1H-imidazoles

A solution of the aldehyde (1 mmol) and threefold excess of ammonium acetate (3 mmol) in methanol (2 mL) was placed in a B5510-DTH (Branson ultrasonic cleaner; Model-5510, frequency 42 KHz with an output power 135 Watts; Branson Ultrasonics, Danbury, CT, USA) sonicator at room temperature. The ultrasonic irradiation was started and a solution of phenylglyoxal monohydrate (1 mmol) in methanol (1 mL) was slowly added dropwise (by a syringe) to the above solution during a period of 15 min. The resulting mixture was continued to irradiate as specified in Table 1. After completion of the reaction (monitored by TLC with an interval of 5 min), the methanol was evaporated under reduced pressure and the crude mass was extracted with ethyl acetate (2 × 5 mL). The combined organic layer was washed with brine (10 mL) and water (10 mL) successively and dried over anhydrous sodium sulfate. The extract was then concentrated, and the crude product was purified using flash chromatography (neutral alumina, 1% triethylamine in methanol) to afford pure compounds.


////////////Imidazole,  Green chemistryUltrasoundHeterocyclesMedicinal chemistry , Azaheterocycles

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