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Spectral properties of ring c oxygenated 4 azafluorenes and 4 azafluorenones the structures of natural onychine derivatives


, : Spectral properties of ring c oxygenated 4 azafluorenes and 4 azafluorenones the structures of natural onychine derivatives. Heterocycles (Tokyo) 27(2): 407-422

4-Azafluorenes bearing a methoxy group at C-5, -6, -7 or -8 and a methyl C-1 or -3 were synthesized by thermolysis of O-crotyloximes of appropriately substituted indan-1-ones. The corresponding azafluorenones were prepared, and the methoxy-1-methyl-4-azafluoren-9-one isomers were O-demethylated. The proton nmr, uv-visible and mass spectra of these compounds support the structures assigned to the more complex azafluorenone alkaloids kinabaline, darienine and macondine, and provide additional guidelines for the structure elucidation of other natural products belonging to this class.

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