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Paper | Special issue | Vol 54, No. 1, 2001, pp.209-215
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)18
Cycloaddition Reactions of Trimethylsilylketene with 8-Azaheptafulvenes and 6-Amino-1-azafulvenes

Kiyo Takaoka, Toyohiko Aoyama,* and Takayuki Shioiri*

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


Trimethylsilylketene smoothly reacts with 8-azaheptafulvenes to give 3,3a-dihydro-3-trimethylsilyl-1-azaazulen-2(1H)-ones, the [8+2] cycloadducts, in excellent yields. Furthermore, trimethylsilylketene also undergoes the [6+2] cycloaddition reaction with 6-amino-1-azafulvenes to afford 1H-pyrrolizin-3(2H)-ones.