Microwave-assisted solvent-free synthesis and antibacterial evaluation of 1-azabicyclo[3.1.0]hexane-3-enes

Abstract

This work described a simple and efficient method for the synthesis of 1-azabicyclo[3.1.0]hexane-3-ene derivatives. arylidenmalononitriles and hydroxylamine hydrochloride in the presence of NaOH, under microwave irradiation and solvent-free conditions produced the titled compounds in good to excellent yields. Using of simple chemicals, short reaction times, and solvent-free conditions, high yields of products, high atomic economy , and eco-friendly are the important advantages of this method. The antibacterial effect of 4-amino-2,6-bis(2,4-dichlorophenyl)-1-azabicyclo[3.1.0]hex-3-ene-3,5-dicarbonitrile was evaluated by minimum inhibitory concentration and disk diffusion method against the standard strains of Staphylococcus aureus and Pseudomonas aeruginosa. Minimum inhibitory concentrations of 2h were 40 and 30 mg/ml for P. aeruginosa and S. aureus respectively and the maximum inhibitory zones were 4 and 5 mm on average, respectively.