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Note | Special issue | Vol 66, No. 1, 2005, pp.675-681
Published online, 29th November, 2005
DOI: 10.3987/COM-05-S(K)69
Are Multicomponent Strecker Reactions of Diketones with Diamines under High Pressure Amenable to Heterocyclic Synthesis?

Koji Kumamoto, Hirokazu Iida, Hiroshi Hamana, Hiyoshizo Kotsuki,* and Kiyoshi Matsumoto,*

*Faculty of Pharmaceutical Sciences, Chiba Institute of Science, 3 Shiomi-cho, Choshi, Chiba 288-0025, Japan

Abstract

Employing double Strecker strategy, two new heterocyclic compounds, 5,6,11,12-tetrahydro-6,11-dimethyldibenzo[b,f][1,4]diazocine-6,11-dicarbonitrile and 1,2,3,4,5,10-hexahydrophenazine-4a,10a-dicarbonitrile, were prepared in one step albeit in low yields. The reaction has proven to be very limited, but such a sterically hindered amine as N-methylaniline underwent Strecker reaction with benzaldehyde and TMSCN to give the corresponding α-amino nitriles.