ABSTRACT
An improved microwave assisted one-pot method for the synthesis of twelve new aryldiazenylchromeno [4,3-b] pyrrolidines via intramolecular azomethine ylide cycloaddition route is described. The method is efficient and advantageous over conventional and solvent-free thermal methods. The stereochemistry of the compounds was confirmed on the basis of various NMR experiments, and finally by single crystal X-ray diffraction data. N-Methyl or ethyl pyrrolidine based heterocycles gave good biological activities.
Subject(s)
Antifungal Agents/chemical synthesis , Antitubercular Agents/chemical synthesis , Benzopyrans/chemical synthesis , Pyrrolidines/chemical synthesis , Antifungal Agents/pharmacology , Antitubercular Agents/pharmacology , Aspergillus fumigatus/drug effects , Aspergillus fumigatus/growth & development , Azo Compounds/chemistry , Benzopyrans/pharmacology , Candida albicans/drug effects , Candida albicans/growth & development , Crystallography, X-Ray , Gram-Negative Bacteria/drug effects , Gram-Negative Bacteria/growth & development , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Microwaves , Molecular Structure , Mycobacterium tuberculosis/drug effects , Mycobacterium tuberculosis/growth & development , Pyrrolidines/pharmacology , Stereoisomerism , Thiosemicarbazones/chemistryABSTRACT
A highly improved one-pot procedure for the synthesis of diazepinones, which incorporate a bioactive quinoline nucleus, under catalyst-, and solvent-free environment has been developed. The method allowed us to achieve the products in high yields without requiring a chromatographic separation. All new quinolyldibenzo[b,e][1,4]diazepinones 6a-h thus obtained were further treated to achieve N10-allylated products 7a-h by a simple allylation. The structure of all new synthesized compounds was established based on elemental analysis, mass, (1)H NMR, (13)C NMR, IR spectral data, 2D NMR experiments, and single crystal X-ray study. From in vitro antimicrobial activity studies it revealed all are active against Gram positive (Streptococcus pneumoniae, Clostridium tetani, and Bacillus subtilis), Gram negative (Salmonella typhi, Vibrio chlolerae and Escherichia coli), M. Tuberculosis H37RV bacteria, and fungus like Candia albicans and Aspergillus fumigatus. All were also found to display good antioxidant activity of a ferric reducing power.