Synthesis and Antimicrobial Evaluation of some Functionalized Heterocycles Derived from Novel Quinolinyl Chalcone

Abstract

The reaction of 3‐acetyl‐4‐hydroxyl‐1‐methylquinolin‐2(1H)‐one (1) with 10‐oxo‐4,6,7,8,9,10‐hexahydropyrazolo[1,5‐a][1]benzothieno[2,3‐d]pyrimidine‐3‐carbaldehyde (2) afforded the novel enone system 3. The latter compound was reacted with some 1,2‐binucleophilic reagents to give pyrazoline derivative 4 and isoxazoline derivative 5. Treatment of chalcone 3 with 1,3‐binucleophilic reagents afforded pyrimidine and thiazine derivatives 6–8. Moreover, reaction of compound 3 with active methylene reagents furnished pyridine, pyran, and cyclohexanone derivatives 9–12. Cyclization of compound 12 by using hydrazine hydrate yielded indazol‐3‐one derivative 13. On the other hand, the cyclocondensation of the enone 3 with 1,4‐dinucleophilic reagents yielded diazepine derivative 14 and triazolothiadiazepine derivative 15.The characterization of the newly synthesized heterocyles were confirmed on the basis of their elemental analysis and spectral data (IR, NMR, and MS). These compounds were also screened for their antibacterial activities.