Novel synthesis of 1,4-thiazin-2-one O-(tert-butyl) oximes and benzo[b][1,4]thiazin-2-one O-(tert-butyl) oximes in the presence of K2CO3/SiO2 |
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| Institution: | 1. Department of Materials and Applied Chemistry, College of Science and Technology, Nihon University, Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan;2. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan;1. State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, and Collaborative Innovation Center for Biotherapy, Chengdu 610041, China;2. State Key Laboratory of Respiratory Disease, Guangzhou Regenerative Medicine and Health Guangdong Laboratory (GRMH-GDL), Guangzhou Institutes of Biomedicine and Health (GIBH), Chinese Academy of Sciences (CAS), Guangzhou 510530, China;3. Institute of Physical Science and Information Technology, Anhui University, Hefei 230601, China;4. Guangdong Zhongsheng Pharmaceutical Co., Ltd, Dongguan, Guangdong 523325, China;1. Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal;2. Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD 21250, USA;1. Non-power Nuclear Technology Collaborative Innovation Center, School of Nuclear Technology and Chemistry & Life Science, Hubei University of Science and Technology, Xianning 437100, China;2. Department of Chemistry, William Paterson University, 300 Pompton Rd, Wayne, NJ 07470, United States;3. Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506, United States;1. Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, Haifa City, 32000, Israel;2. Institut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106, Braunschweig, Germany;1. Department of Chemistry, Lancaster University, Bailrigg, Lancaster LA1 4YB, United Kingdom;2. Oncology, IMED Biotech Unit, AstraZeneca, Cambridge CB10 1XL, United Kingdom |
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| Abstract: | A simple and efficient method was developed for the synthesis of 1,4-thiazin-2-one O-(tert-butyl) oximes and benzob]1,4]thiazin-2-one O-(tert-butyl) oximes from N-tert-butoxy acyl imidoyl bromides and 2-aminothiols in the presence of K2CO3/SiO2. Twenty five novel compounds were readily synthesized in excellent yields using this procedure. The products possessed Z-stereochemistry with regard to the C N double bond. The reaction proceeded with initial substitution of bromine in the N-tert-butoxy acyl imidoyl bromides by mercapto groups in the presence of K2CO3/SiO2, and subsequent intramolecular Schiff base formation. |
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| Keywords: | 1 4-Thiazin-2-one oximes Heterogeneous reaction One-pot reaction |
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