Photocycloaddition of Benzothiazole-2-thiones to Alkenes
| Autor: | Akira Hosomi, Yo-ichi Mori, Takehiko Nishio, Ikuo Iida |
|---|---|
| Rok vydání: | 1994 |
| Předmět: |
chemistry.chemical_classification
Addition reaction Bicyclic molecule Chemistry Alkene Organic Chemistry Crystal structure Ring (chemistry) Biochemistry Medicinal chemistry Catalysis Cycloaddition Inorganic Chemistry chemistry.chemical_compound Benzothiazole Drug Discovery Molecule Physical and Theoretical Chemistry |
| Zdroj: | Helvetica Chimica Acta. 77:981-987 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.19940770410 |
| Popis: | The photocycloaddition of benzothiazole-2-thiones to electron-rich and aryl-substituted alkenes are described. Irradiation of N-unsubstituted benzothiazole-2-thione (1) in the presence of alkenes 3 gave 2-(2′-mercaptoalkyl)benzothiazoles 4, and 2-substituted benzothiazoles 5 and 6 (in the case of 3a and 3h, resp.) through the ring cleavage of an intermediate 2-aminothietane (Schemes 1 and 3). The latter was formed by [2+2] cycloaddition of the CS bond of 1 and the CC bond of 3. Irradiation of N-methylbenzothiazole-2-thione (2) and 2-methylpropene (3a) gave the spiro-1,3-dithiane 8, 1,2,6-benzodithiazocin-5-one 9, and disulfide 10. The structure of 9 was established by X-ray crystal-structure analysis. |
| Databáze: | OpenAIRE |
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