A facile synthesis of 10-methoxy-4,8-dinitro-6H-benzothieno[2,3-c]chromen-6-one

3-Methoxy-5-nitrobenzaldehyde undergoes Knoevenagel reaction with malonic acid to give 3-methoxy-5-nitrocinnamic acid (I). Treatment of I with thionyl chloride yielded 3-chloro-5-methoxy-7-nitrobenzo[b]thiophene-2-carbonyl chloride (II) in 45 % yield. The reaction of II with 2-nitrophenol in benzene...

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Published in:Journal of the Serbian Chemical Society 2004-01, Vol.69 (7), p.527-532
Main Authors: SANDEEP BURUDKAR, SANJAY BHISE, FREDDY H. HAVALDAR
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Language:English
Subjects:
antibacterial activity
cinnamic acid
coumarin
photolytic cyclization
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creator SANDEEP BURUDKAR
SANJAY BHISE
FREDDY H. HAVALDAR
description 3-Methoxy-5-nitrobenzaldehyde undergoes Knoevenagel reaction with malonic acid to give 3-methoxy-5-nitrocinnamic acid (I). Treatment of I with thionyl chloride yielded 3-chloro-5-methoxy-7-nitrobenzo[b]thiophene-2-carbonyl chloride (II) in 45 % yield. The reaction of II with 2-nitrophenol in benzene gave 2-nitrophenyl 3-chloro-5-methoxy-7-nitrobenzo[b]thiophene-2-carboxylate (IIIa) in 65 % yield. Finally, dehydrochlorinative photocyclization of IIIa in acetone in the presence of the base triethylamine afforded 10-methoxy-4,8-dinitro-6H-benzothieno[2,3-c]chromen-6-one (IVa). Thus, a series of derivatives IVa-i were synthesized in excellent yields. The structures of the obtained products were characterized by IR and 1H-NMR spectroscopy, as well as elemental analysis. Their purity was ascertained by chromatographic analysis. All the compounds were tested for their antibacterial activity against S. aureus, E. coli, B. subtilis and S. typhosa.
doi_str_mv 10.2298/JSC0407527H
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subjects antibacterial activity
cinnamic acid
coumarin
photolytic cyclization
title A facile synthesis of 10-methoxy-4,8-dinitro-6H-benzothieno[2,3-c]chromen-6-one
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