دورية أكاديمية
Ringerweiterungen und Ringverengungen bei der Umsetzung von 1,3- Oxazolidin-2,4-dionen und 1,3-Thiazolidin-2,4-dion mit 3-Amino-2H-azirinen
| العنوان: | Ringerweiterungen und Ringverengungen bei der Umsetzung von 1,3- Oxazolidin-2,4-dionen und 1,3-Thiazolidin-2,4-dion mit 3-Amino-2H-azirinen |
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| المؤلفون: | Ametamey, Simon M, Heimgartner, Heinz |
| المصدر: | Ametamey, Simon M; Heimgartner, Heinz (1990). Ringerweiterungen und Ringverengungen bei der Umsetzung von 1,3- Oxazolidin-2,4-dionen und 1,3-Thiazolidin-2,4-dion mit 3-Amino-2H-azirinen. Helvetica Chimica Acta, 73(5):1314-1328. |
| بيانات النشر: | Wiley-Blackwell |
| سنة النشر: | 1990 |
| المجموعة: | University of Zurich (UZH): ZORA (Zurich Open Repository and Archive |
| مصطلحات موضوعية: | Department of Chemistry, 540 Chemistry, Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
| الوصف: | The reaction of 3-amino-2H-azirines 1 and 1,3-oxazolidine-2,4-diones 2 in MeCN at room temperature leads to 3,4-dihydro-3-(2-hydroxyacetyl)-2H-imidazol-2-ones 3 in good yield (Scheme 2, Table I). A reaction mechanism proceeding via ring enlargement of the bicyclic zwitterion A to give B, followed by transannular ring contraction to C, is proposed for the formation of 3. This mechanism is in accordance with the result of the reaction of 2a and the 15N-labelled 1a*: in the isolated product 3a*, only N(3) is labelled (Scheme 2). The analogous reaction of 1 and 1,3-thiazolidine-2,4-dione (5) is more complex (Schemes 4 and 5,Table 2). Besides the expected 3,4-dihydro-3-(2-mercaptoacetyl)-2H-imidazol-2-ones 7, 5-amino-3,4-dihydro-2H-imidazol-2-ones of type 8 and/or N-(1,4-thiazin-2-ylidene)ureas 9 are formed. In the case of 2-(dimethylamino)-1- azaspiro[2.3]hex-1-ene (1d), the postulated eight-membered intermediate 6d could be isolated. Its structure as well as that of 9f has been determined by X-ray structure analysis. A reaction mechanism for the formation of the 1,4-thiazine derivatives of type 9 is proposed in Scheme 6. |
| نوع الوثيقة: | article in journal/newspaper |
| وصف الملف: | application/pdf |
| اللغة: | German |
| تدمد: | 0018-019X |
| العلاقة: | https://www.zora.uzh.ch/id/eprint/94221/1/134_Ametamey_HCA_1990.pdfTest; urn:issn:0018-019X |
| DOI: | 10.5167/uzh-94221 |
| DOI: | 10.1002/hlca.19900730520 |
| الإتاحة: | https://doi.org/10.5167/uzh-9422110.1002/hlca.19900730520Test https://www.zora.uzh.ch/id/eprint/94221Test/ https://www.zora.uzh.ch/id/eprint/94221/1/134_Ametamey_HCA_1990.pdfTest |
| حقوق: | info:eu-repo/semantics/closedAccess |
| رقم الانضمام: | edsbas.20445DE4 |
| قاعدة البيانات: | BASE |
| تدمد: | 0018019X |
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| DOI: | 10.5167/uzh-94221 |