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Paper | Regular issue | Vol 24, No. 10, 1986, pp.2835-2840
Published online, 1st January, 1970
DOI: 10.3987/R-1986-10-2835
New Syntheses of 1-Amino- and 1-(2-Aminoethyl)-2,6-dicyanopiperidines and Diazabicyclo Compounds by a Strecker Reaction Using Glutaraldehyde and Diamines, and Their Stereochemistry

Kazumasa Takahashi,* Akira Tachiki, Katsuyuki Ogura, and Hirotada Iida

*Deparment of Synthetic Chemistry, Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

An efficient sequence proposed here involves a simple Strecker reaction of glutaraldehyde with hydrazine or 1,2-diaminoethane, which gives 1-amino- or 1-(2-aminoethyl)-2,6-dicyanopiperidines, 2-cyano-1,7-diazabicyclo[4.3.0]nonane, and 10-cyano-1,4-diazabicyclo[4.4.0]decan-5-one. Their stereochemistry is also elucidated. Moreover, treatment of l-amino-2,6-dicyanopiperidine and phthaloyl dichloride in the presence of 4-(N,N-dimethylamino)pyridine quantitatively gives 1-phthalimido-2,6-dicyanopiperidine.