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Paper | Special issue | Vol 77, No. 1, 2009, pp.471-481
Published online, 25th August, 2008
DOI: 10.3987/COM-08-S(F)44
Preparation of New Nitrogen-bridged Heterocycles. 64. A Smooth Formation of 2,4-Diarylpyrido[2,3-b]indolizine-10-carbonitrile Derivatives

Akikazu Kakehi,* Hiroyuki Suga, and Shuichi Sato

*Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan


The syntheses of the title compounds from the reactions of 2-amino-3-(arylcarbonyl)indolizine-1-carbonitriles with various acetophenones in the presence of strong base were investigated. When the reactions were carried out between 2-aminoindolizines and 1.2-equimolar amounts of acetophenones, the yields for the target molecules were low or very low. However, when a large excess of acetophenones were used without any solvent or in as small as amount of solvent as possible, their yields were considerably improved. The smooth hydrolysis of the 10-cyano group to the carbamoyl one was also observed.