Synthesis and Antimicrobial Studies of Novel Imidazole Containing Bisazetidinones and Bisthiazolidinone Derivatives

A simple, practical, and efficient approach to new series of imidazole containing bisazetidinones (7a, 7b, 7c, 7d, 7e, 7f, 7g, 7h, 7i, 7j and 9a, 9b, 9c, 9d, 9e, 9f, 9g, 9h, 9i, 9j) was prepared by Staudinger [2+2] cycloaddition reaction, and bisthiazolidinones (8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j and 10a, 10b, 10c, 10d, 10e, 10f, 10g, 10h, 10i, 10j) were obtained by cyclization of bisimines with thioglycolic acid. The bisimines (5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j and 6a, 6b, 6c, 6d, 6e, 6f, 6g, 6h, 6i, 6j) were synthesized by the condensation of 3-(1-(3-aminobenzyl)-4, 5-dihydro-1H-imidazol-2-yl) aniline (3, 4) with a series of different substituted aromatic aldehydes. All the newly synthesized target compounds were evaluated for their in vitroantimicrobial activity against two Gram-positive bacteria and two Gram-negative bacteria. Additionally, these synthesized compounds were tested for their antifungal activities. Few compounds showed very good antibacterial and antifungal activity.