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Paper | Special issue | Vol 74, No. 1, 2007, pp.721-730
Published online, 12th October, 2007
DOI: 10.3987/COM-07-S(W)57
A Facile and Convenient Synthetic Method for 2-Bis(trifluoroacetyl)methylene- and 2-Trifluoroacetylmethylene-2,3-dihydro-3-methylthiazoles

Norio Ota, Etsuji Okada,* Yasuhiro Kamitori, Dai Shibata, and Maurice Médebielle

*Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan

Abstract

2,3-Dimethylthiazolium iodides (1) reacted easily with trifluoroacetic anhydride in the presence of pyridine to give 2-bis(trifluoroacetyl)methylene-2,3-dihydro-3-methylthiazoles (2) in excellent yields. Deacylation of 2 proceeded readily in moderate to high yields by acid catalyst such as silica gel and aqueous hydrochloric acid to afford the corresponding 2-trifluoroacetylmethylene-2,3-dihydro-3-methylthiazoles (3), which were smoothly reconverted into diacylated compounds (2) with trifluoroacetic anhydride. The highly poralized structure of 2 was also briefly discussed.