An Efficient and Simple One-Pot Synthesis of Novel 2-Amino-5-aza-6-(dinitrilomethylene)-4,7,7-trimethylbicyclo[2.2.2]octane-1,3-dicarbo-nitrile and its Crystal Structure

Abstract  

The title compound was prepared by the reaction of 4-methyl-pent-3-en-2-one and malononitrile, at room temperature, in the presence of indium-triflate and triethylamine. The structure of the molecule was established by spectral analysis and X-ray diffraction studies. The compound crystallizes in the monoclinic space group C2/c with unit cell parameters: a = 14.269 (2), b = 10.141 (2), c = 19.743 (3) ?, β = 95.523(4)°, Z = 8. The crystal structure was solved by direct methods and refined to R = 0.0526 for 2,690 observed reflections. The isoquinuclidine rings adopt boat conformation. The molecules in the unit cell are arranged in layers. The crystal structure is stabilized by N–H⋯N interactions.