A facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [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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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2004-01-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2004/0352-51390407527H.pdf |
| _version_ | 1818950007780278272 |
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| author | Havaldar F.H. Bhise S. Burudkar S. |
| author_facet | Havaldar F.H. Bhise S. Burudkar S. |
| author_sort | Havaldar F.H. |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-20T09:11:45Z |
| format | Article |
| id | doaj.art-5d133053583341bb99cc780735b41d74 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-20T09:11:45Z |
| publishDate | 2004-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-5d133053583341bb99cc780735b41d742022-12-21T19:45:32ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212004-01-0169752753210.2298/JSC0407527H0352-51390407527HA facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [2,3-c]chromen-6-oneHavaldar F.H.0Bhise S.1Burudkar S.2Nadkarny-Sacasa Research Laboratory, Department of Chemistry, St. Xavier's College, Mumbai, IndiaNadkarny-Sacasa Research Laboratory, Department of Chemistry, St. Xavier's College, Mumbai, IndiaNadkarny-Sacasa Research Laboratory, Department of Chemistry, St. Xavier's College, Mumbai, India3-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.http://www.doiserbia.nb.rs/img/doi/0352-5139/2004/0352-51390407527H.pdfcoumarincinnamic acidantibacterial activityphotolytic cyclization |
| spellingShingle | Havaldar F.H. Bhise S. Burudkar S. A facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [2,3-c]chromen-6-one Journal of the Serbian Chemical Society coumarin cinnamic acid antibacterial activity photolytic cyclization |
| title | A facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [2,3-c]chromen-6-one |
| title_full | A facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [2,3-c]chromen-6-one |
| title_fullStr | A facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [2,3-c]chromen-6-one |
| title_full_unstemmed | A facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [2,3-c]chromen-6-one |
| title_short | A facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [2,3-c]chromen-6-one |
| title_sort | facile synthesis of 10 methoxy 4 8 dinitro 6h benzo 2 3 c chromen 6 one |
| topic | coumarin cinnamic acid antibacterial activity photolytic cyclization |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2004/0352-51390407527H.pdf |
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