Abstract

[3+2] Cycloaddition reactions of 5-azido-4-trifluoromethyl-1,3-azoles with various CC multiple bond systems are described. On reaction of 5-azido-4-trifluoromethylthiazoles 2 with 2,3-dimethylbuta-1,3-diene no [3+2] cycloaddition products could be isolated, 5,6-dihydro-2 H-pyrane 19 was formed exclusively. Photolysis of 1,2,3-triazoles 23, 24, obtained from 2 and electron deficient alkynes, yields imidazo[5,1-b]thiazoles 28. This photoreaction can be interpreted mechanistically as a “Thio-Cornforth-Reaction”.

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