Pekcan, Sare; Heimgartner, Heinz (1988). N-(1,3-Thiazol-5(4H)-yliden)amine aus 1,3-dipolaren Cycloadditionen von Aziden mit 1,3-Thiazo1-5(4H)-thionen. Helvetica Chimica Acta, 71(7):1673-1680.
Abstract
Organic azides 5 and 4,4-dimethyl-2-phenyI-1,3-thiazol-5(4H)-thione (2) in toluene at 90° react to give the corresponding N-(1,3-thiazol-5(4H)-ylidene)amines ( = 1,3-thiazol-5(4H)-imines) 6 in good yield (Table). A reaction mechanism for the formation of these scarcely investigated thiazole derivatives is formulated in Scheme 3: 1,3-Dipolar azide cycloaddition onto the C=S group of 2 leads to the 1:1 adduct C. Successive elimination of N2 and S yields 6, probably via an intermediate thiaziridine E.
| Other titles: | N-(1,3-Thiazol-5(4H)-ylidene)amines via 1,3-Dipolar Cycloaddition of Azides and 1,3-Thiazol-5(4H)-thiones |
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| Item Type: | Journal Article, refereed, original work |
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| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
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| Dewey Decimal Classification: | 540 Chemistry |
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| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry |
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| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
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| Language: | German |
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| Date: | 1988 |
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| Deposited On: | 14 May 2014 08:46 |
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| Last Modified: | 11 Mar 2025 02:37 |
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| Publisher: | Wiley-Blackwell |
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| ISSN: | 0018-019X |
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| Funders: | Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La roche AG, Basel |
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| OA Status: | Closed |
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| Publisher DOI: | https://doi.org/10.1002/hlca.19880710713 |
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| Project Information: | - Funder: SNSF
- Grant ID:
- Project Title: Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
- Funder:
- Grant ID:
- Project Title: F. Hoffmann-La roche AG, Basel
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Pekcan, Sare