Synthesis of amide‐linked benzazolyl isoxazoles adopting green methods and evaluation as antimicrobials
Some new benzoxazolyl isoxazoles, benzothiazolyl isoxazoles and benzimidazolyl isoxazoles connected by amide bonds (7‐9) were prepared from N‐benzazolylcarbamoylmethylcinnamamides (1‐3) adopting eco‐friendly synthetic methodologies. In fact, cycloaddition of nitrile oxide generated from araldoxime u...
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| Veröffentlicht in: | Journal of heterocyclic chemistry 2020-04, Vol.57 (4), p.1882-1892 |
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| container_end_page | 1892 |
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| container_issue | 4 |
| container_start_page | 1882 |
| container_title | Journal of heterocyclic chemistry |
| container_volume | 57 |
| creator | Sowdari, Jyothi Thata, Sreenivasulu Gudi, Yamini Venkatapuram, Padmavathi Adivireddy, Padmaja |
| description | Some new benzoxazolyl isoxazoles, benzothiazolyl isoxazoles and benzimidazolyl isoxazoles connected by amide bonds (7‐9) were prepared from N‐benzazolylcarbamoylmethylcinnamamides (1‐3) adopting eco‐friendly synthetic methodologies. In fact, cycloaddition of nitrile oxide generated from araldoxime using iodosobenzene and cetyltrimethylammonium bromide to 1‐3 followed by treatment with iodine in dimethyl sulfoxide led to the formation of title compounds with good yields and in shorter reaction times. The structures of all the synthesized compounds were confirmed by spectral parameters, viz, IR, NMR, and mass spectra and were assayed for antimicrobial activity. Among all the tested compounds, 8a and 8c displayed excellent antibacterial activity, whereas 9a and 9c showed promising antifungal activity. |
| doi_str_mv | 10.1002/jhet.3916 |
| format | Article |
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In fact, cycloaddition of nitrile oxide generated from araldoxime using iodosobenzene and cetyltrimethylammonium bromide to 1‐3 followed by treatment with iodine in dimethyl sulfoxide led to the formation of title compounds with good yields and in shorter reaction times. The structures of all the synthesized compounds were confirmed by spectral parameters, viz, IR, NMR, and mass spectra and were assayed for antimicrobial activity. 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In fact, cycloaddition of nitrile oxide generated from araldoxime using iodosobenzene and cetyltrimethylammonium bromide to 1‐3 followed by treatment with iodine in dimethyl sulfoxide led to the formation of title compounds with good yields and in shorter reaction times. The structures of all the synthesized compounds were confirmed by spectral parameters, viz, IR, NMR, and mass spectra and were assayed for antimicrobial activity. Among all the tested compounds, 8a and 8c displayed excellent antibacterial activity, whereas 9a and 9c showed promising antifungal activity.</description><subject>Cetyltrimethylammonium bromide</subject><subject>Cycloaddition</subject><subject>Dimethyl sulfoxide</subject><subject>Fungicides</subject><subject>Iodine</subject><subject>Mass spectra</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kEtOwzAQhi0EEqWw4AaWWLFI60ecxxJVQEGVWFAkdpYTT1qX1C5xCqQrjsAZOQkOZctqXt_M_PoROqdkRAlh49US2hHPaXKABjSPeSRozg_RIMxYRAV7PkYn3q9CSXmaDpB57Gy7BG88dhVWa6Ph-_OrNvYFNC7A7tTO1V2NjXcffQoeK-02rbELvGgALF5Du3Q6tK3G8KbqrWqNs1j1ndasTdm4wqjan6KjKgQ4-4tD9HRzPZ9Mo9nD7d3kahaVLE-TSPMqLmnBSyEoFwI0yYARFeRmrCRJwoqCsjCIGeSUapFlFdOMABVZComO-RBd7O9uGve6Bd_Klds2NryUjGdpHkyIs0Bd7qkgz_sGKrlpzFo1naRE9k7K3knZOxnY8Z59NzV0_4Pyfno9_934AeMDd8g</recordid><startdate>202004</startdate><enddate>202004</enddate><creator>Sowdari, Jyothi</creator><creator>Thata, Sreenivasulu</creator><creator>Gudi, Yamini</creator><creator>Venkatapuram, Padmavathi</creator><creator>Adivireddy, Padmaja</creator><general>John Wiley & Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-3448-1423</orcidid><orcidid>https://orcid.org/0000-0002-2991-803X</orcidid><orcidid>https://orcid.org/0000-0003-4015-8163</orcidid></search><sort><creationdate>202004</creationdate><title>Synthesis of amide‐linked benzazolyl isoxazoles adopting green methods and evaluation as antimicrobials</title><author>Sowdari, Jyothi ; Thata, Sreenivasulu ; Gudi, Yamini ; Venkatapuram, Padmavathi ; Adivireddy, Padmaja</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2976-d3f4c1b3c551355ed08e20a21382c0662bb1235542e911d588f2d20e1587e6d43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Cetyltrimethylammonium bromide</topic><topic>Cycloaddition</topic><topic>Dimethyl sulfoxide</topic><topic>Fungicides</topic><topic>Iodine</topic><topic>Mass spectra</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sowdari, Jyothi</creatorcontrib><creatorcontrib>Thata, Sreenivasulu</creatorcontrib><creatorcontrib>Gudi, Yamini</creatorcontrib><creatorcontrib>Venkatapuram, Padmavathi</creatorcontrib><creatorcontrib>Adivireddy, Padmaja</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sowdari, Jyothi</au><au>Thata, Sreenivasulu</au><au>Gudi, Yamini</au><au>Venkatapuram, Padmavathi</au><au>Adivireddy, Padmaja</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of amide‐linked benzazolyl isoxazoles adopting green methods and evaluation as antimicrobials</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><date>2020-04</date><risdate>2020</risdate><volume>57</volume><issue>4</issue><spage>1882</spage><epage>1892</epage><pages>1882-1892</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>Some new benzoxazolyl isoxazoles, benzothiazolyl isoxazoles and benzimidazolyl isoxazoles connected by amide bonds (7‐9) were prepared from N‐benzazolylcarbamoylmethylcinnamamides (1‐3) adopting eco‐friendly synthetic methodologies. 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| identifier | ISSN: 0022-152X |
| ispartof | Journal of heterocyclic chemistry, 2020-04, Vol.57 (4), p.1882-1892 |
| issn | 0022-152X 1943-5193 |
| language | eng |
| recordid | cdi_proquest_journals_2387915248 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Cetyltrimethylammonium bromide Cycloaddition Dimethyl sulfoxide Fungicides Iodine Mass spectra NMR Nuclear magnetic resonance |
| title | Synthesis of amide‐linked benzazolyl isoxazoles adopting green methods and evaluation as antimicrobials |
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