On a New Unexpected Benzoxazino-Benzoxazine Derivative

The reaction between 2-amino-5-nitrophenol and 1,2-cyclohexanedione in ethanol leads to formation, in addition to corresponding propellane, of 3. The X-ray diffraction, NMR and IR studies allowed to solve the structure of molecules. It has been shown that planar nitrobenzoxazine groups are oriented to each other perpendicularly with a chair conformation of the cyclohexyl unit. The possible mechanism of reaction leading to 3 is discussed.