Microwave induced diastereoselective synthesis of spiro[indole-oxiranes] and their conversion to spiro[indole-pyrazoles].
The microwave induced diastereoselective synthesis of spiro[3H-indole-3,2'-oxiranes]-3'-benzoyl-2 (1H)-one is reported. Epoxidation of 3-aroylmethylene indole-2-one 1 with alkaline H2O2 under microwave irradiation in an open vessel under controlled conditions yields a diastereomeric pair of spiro[3H-indole-3,2'-oxiranes]-3'-benzoyl-2 (1H) ones 2 and 3 in 65-85% yield. The stereoselectivity depends upon the reaction time and power output. The spiro[indole-pyrazoles] 4 have been synthesised by the reaction of 2 with hydrazine hydrate. Under the same condition 3 gave the mixture of products. All synthesised compounds have been screened in vitro for their antifungal activity against Rhizoctonia solani, Fusarium oxysporum and Collectotrichum capsici and antitubercular activity against Mycobacterium tuberculosis.
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D005658:Fungi / Q000187:drug effects; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D011720:Pyrazoles / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D000935:Antifungal Agents; D000995:Antitubercular Agents; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007211:Indoles; D011720:Pyrazoles