Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reaction
Reaction of o-azidobenzenesulfonamides with ethyl carbonochloridate afforded the corresponding amide derivatives, which gave 3-ethoxy-1,2,4-benzothiadiazine 1,1-dioxides through an intramolecular aza-Wittig reaction. The reaction was found to be general through the synthesis of a number of benzothia...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.54 |
| _version_ | 1818732587984617472 |
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| author | Krishna C. Majumdar Sintu Ganai |
| author_facet | Krishna C. Majumdar Sintu Ganai |
| author_sort | Krishna C. Majumdar |
| collection | DOAJ |
| description | Reaction of o-azidobenzenesulfonamides with ethyl carbonochloridate afforded the corresponding amide derivatives, which gave 3-ethoxy-1,2,4-benzothiadiazine 1,1-dioxides through an intramolecular aza-Wittig reaction. The reaction was found to be general through the synthesis of a number of benzothiadiazine 1,1-dioxides. Acid-catalyzed hydrolysis of 3-ethoxy-1,2,4-benzothiadiazine 1,1-dioxides furnished the 2-substituted benzothiadiazine-3-one 1,1-dioxides in good yields and high purity, which is the core moiety of RSV inhibitors. |
| first_indexed | 2024-12-17T23:35:57Z |
| format | Article |
| id | doaj.art-7423c9a794d0439fabda15d7d47722ba |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T23:35:57Z |
| publishDate | 2013-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-7423c9a794d0439fabda15d7d47722ba2022-12-21T21:28:33ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-03-019150350910.3762/bjoc.9.541860-5397-9-54Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reactionKrishna C. Majumdar0Sintu Ganai1Department of Chemistry, University of Kalyani, Kalyani 741235, W.B IndiaDepartment of Chemistry, University of Kalyani, Kalyani 741235, W.B IndiaReaction of o-azidobenzenesulfonamides with ethyl carbonochloridate afforded the corresponding amide derivatives, which gave 3-ethoxy-1,2,4-benzothiadiazine 1,1-dioxides through an intramolecular aza-Wittig reaction. The reaction was found to be general through the synthesis of a number of benzothiadiazine 1,1-dioxides. Acid-catalyzed hydrolysis of 3-ethoxy-1,2,4-benzothiadiazine 1,1-dioxides furnished the 2-substituted benzothiadiazine-3-one 1,1-dioxides in good yields and high purity, which is the core moiety of RSV inhibitors.https://doi.org/10.3762/bjoc.9.54benzothiadiazine-3-one 1,1-dioxide3-ethoxy-1,2,4-benzothiadiazine 1,1-dioxideintramolecular aza-Wittig reactionsultam |
| spellingShingle | Krishna C. Majumdar Sintu Ganai Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reaction Beilstein Journal of Organic Chemistry benzothiadiazine-3-one 1,1-dioxide 3-ethoxy-1,2,4-benzothiadiazine 1,1-dioxide intramolecular aza-Wittig reaction sultam |
| title | Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reaction |
| title_full | Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reaction |
| title_fullStr | Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reaction |
| title_full_unstemmed | Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reaction |
| title_short | Facile synthesis of benzothiadiazine 1,1-dioxides, a precursor of RSV inhibitors, by tandem amidation/intramolecular aza-Wittig reaction |
| title_sort | facile synthesis of benzothiadiazine 1 1 dioxides a precursor of rsv inhibitors by tandem amidation intramolecular aza wittig reaction |
| topic | benzothiadiazine-3-one 1,1-dioxide 3-ethoxy-1,2,4-benzothiadiazine 1,1-dioxide intramolecular aza-Wittig reaction sultam |
| url | https://doi.org/10.3762/bjoc.9.54 |
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