Reactions of Trimethylsilylthiazoles with Ketens: A New Route to Regioselective Functionalisation of the Thiazole Ring

DOI: 10.1039/c39810000655

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 655 - 656 (1981)

Update date:2022-07-29

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Authors:

Medici, Alessandro

Pedrini, Paola

Dondoni, Alessandro

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Article abstract of DOI:10.1039/c39810000655

2-Trimethylsilylthiazole (2) and 2,5-bis(trimethylsilyl)thiazole (6) undergo ipso-substitution of the 2-SiMe3 group with various ketens affording the thiazolyl-trimethylsiloxy-ethylenes (3) and (7), respectively, which are hydrolysed to the 2-acylthiazoles (4), whereas 5-trimethylsilylthiazole (8) undergoes attack at C-2 by dichloroketen giving the Michael-type adduct 2-dichloroacetyl-5-trimethylsilylthiazole (9c).

Full text of DOI:10.1039/c39810000655

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