Publication: N-(1,3-Thiazol-5(4H)-yliden)amine aus 1,3-dipolaren Cycloadditionen von Aziden mit 1,3-Thiazo1-5(4H)-thionen
N-(1,3-Thiazol-5(4H)-yliden)amine aus 1,3-dipolaren Cycloadditionen von Aziden mit 1,3-Thiazo1-5(4H)-thionen
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Pekcan, S., & Heimgartner, H. (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. https://doi.org/10.1002/hlca.19880710713
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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.
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- Pekcan, Sare
- Heimgartner, Heinz
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Pekcan, S., & Heimgartner, H. (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. https://doi.org/10.1002/hlca.19880710713
