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A series of fluorinated spiro[1,5-benzothiazepin-2,3′[3′H]-indol]-2′(1′H)-ones have been prepared by the reaction of 2-aminobenzene-thiols with 1,3-dihydro-3-[2-phenyl/(4-fluorophenyl)-2-oxoethylidene)-indol-2(1H)-ones (I) under microwave irradiation in open vessels using ethylene glycol as energy transfer medium and thermally in absolute ethanol saturated with hydrogen chloride gas. The comparative studies indicated that the microwave assisted organic synthesis has advantages of significantly reduced reaction time, improved yields and cleaner reactions as compared to the conventional method. All synthesized compounds have been characterized by analytical and spectral data and were screened for their antifungal activity against Alternaria alternata and Fusarium oxysporium and antitubercular activity against Mycobacterium tuberculosisIVb (R = F, X = F) and IVe (R = F, X = CH₃) have shown …