One-Pot Domino Reaction: Direct Access to Polysubstituted 1,4-Benzothiazine 1,1-Dioxide via Water-Gas Shift Reaction Utilizing DMF/H 2 O.
| Autor: | Sharma Y; Division of Medicinal Chemistry, CSIR-Institute of Microbial Technology, Chandigarh 160036, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India., Pawar GP; Division of Medicinal Chemistry, CSIR-Institute of Microbial Technology, Chandigarh 160036, India., Chaudhari VD; Division of Medicinal Chemistry, CSIR-Institute of Microbial Technology, Chandigarh 160036, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2023 Jan 06; Vol. 88 (1), pp. 701-710. Date of Electronic Publication: 2022 Dec 20. |
| DOI: | 10.1021/acs.joc.2c02171 |
| Abstrakt: | Benzothiazine 1,1-dioxide (BTDO) is a privileged chemical motif, and its metal-free domino access is in high demand. Current BTDO production methods require costly metal catalysts or harsh reaction conditions. A facile domino approach to BTDO via a water-gas shift reaction (WGSR) employing sodium 2-nitrobenzenesulfinates and α-bromo ketones is presented. This strategy is cost-effective and environmentally beneficial. The optimized reaction conditions demonstrated remarkable chemical tolerance to a wide range of electrically and sterically varied substituents on both coupling partners. |
| Databáze: | MEDLINE |
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