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
| Autor: | Shigeru Shimada, Kenshiro Tashiro, Akihiko Ouchi, Tadashi Aoyama, Mamiko Hayakawa |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Tert butyl Schiff base Bromine Double bond 010405 organic chemistry Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Intramolecular force Drug Discovery |
| Zdroj: | Tetrahedron Letters. 60:1493-1497 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2019.04.053 |
| Popis: | A simple and efficient method was developed for the synthesis of 1,4-thiazin-2-one O-(tert-butyl) oximes and benzo[b][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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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