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Paper | Regular issue | Vol 45, No. 11, 1997, pp.2197-2208
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7948
Synthesis of Mesomeric Betaines, Quinoliziniumides, via Back-donated 1,6-Cyclization

Yoshiro Matsuda,* Keisuke Katou, Takanobu Nishiyori, Takashi Uemura, and Maki Urakami

*Faculty of Environmental Studies, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


The reaction of 3-aminopyridinium salts (4) with polarized olefins (2a, b, 3) in the presence of triethylamine yielded the corresponding 3-aminopyridinium N-allylides (5a). Thermolysis of 3-aminopyridinium N-allylides (5a-c, h-j, l-n) in refluxing xylene afforded the 1,5-dipolar cyclization products, 8-aminoindolizines (6) togeher with the back-donated 1,6-cyclization products quinoliziniumides (7). In addition, thermolysis of N-allylides (5a-c, h-j, l-n) in refluxing AcOH gave quinoliziniumides (7).