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SPECTRAL PROPERTIES OF RING-C-OXYGENATED 4-AZAFLUORENES AND 4-AZAFLUORENONES. THE STRUCTURES OF NATURAL ONYCHINE DERIVA TIVES

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1987-09-30
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Tadic, Dragana
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SPECTRAL PROPERTIES OF RING-C-OXYGENATED 4-AZAFLUORENES AND 4-AZAFLUORENONES. THE STRUCTURES OF NATURAL ONYCHINE DERIVA TIVES
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Author
  • Tadic, Dragana;
  • Cassels Niven, Bruce;
  • Cavé, André;
Abstract
4-Azafluorenes bcaring a methoxy group at C-5, -6, -7 or -8 and a methyl at Col or -3 were synthesized by thermolysis of O-crotyloximes of appropriately substitutcd indan-I-ones. The corrcsponding azalluorenones were prepared, and the methoxy-I-methyl-4-azafluoren-9-one isomers were 0- demethylated. The proton nmr, uv-visible and mass spcctra of these compounds support the structures assigned to the more complex azafluorenone alkaloids kinabaline, darienine and macondine, and provide addiLional guidelines for the structure elucidation of other natural products bclonging to this class.
Patrocinador
We are graleful lo Dr D. Davousl for lhe 500 MHz lH nmr spectra and Dr l.A. Pinheiro for work al 200 MHz. D.T. was supported in part by a fellowship from the French government.
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URI: https://repositorio.uchile.cl/handle/2250/119597
ISSN: 0385-5414
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HETEROCYCLES, Vol. 27, No. 1, 1988.
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