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Communication | Regular issue | Vol 4, No. 5, 1976, pp.957-962
Published online, 1st January, 1970
DOI: 10.3987/R-1976-05-0957
Azafulvenes 3. Cycloaddition Reaction of 6-Amino-1-azafulvene to Electron-deficient Olefin and Acetylene

Sigeo Mori, Masanori Watanabe, Shoji Kajigaeshi, and Shuji Kanemasa*

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


6-Amino-1-azafulvene (1) reacted with the electron-deficient olefins such as acrylate, vinyl ketone, acrylonitrile and N-arylmaleimide affording the regio- and stereospecific [6+2] cycloadducts (4a-4g), some of which were readily deaminated to give the corresponding 3H-pyrrolizines (5a-5c). On the other hand, 1 gave the 1:2 cycloadduct with acetylenedicarboxylate.