Journal of the Chemical Society. Perkin transactions I p. 535 - 539 (1980)
Update date:2022-08-05
Topics:
Acheson, R. Morrin
Letcher, Roy M.
Procter, Garry
1,2,6,7,8,9-Hexahydropyrrolo<3,2,1-jk>carbazole with dimethyl acetylenedicarboxylate in aqueous acetic acid gave four complex products, the structures of which have been correlated with their 13C n.m.r. and other spectra.The carbazole was hydrolysed as an enamine to the corresponding amino-ketone, and the reactions of the latter with the acetylenic ester examined.It is concluded that the acetylene first attacks the carbazole at position 5b, and ring-opening to an amino-ketone and conversion to the complex products follow.An intramolecular dehydrogenation of cyclohexanone to a cyclohex-2-enone grouping by an enamine residue which is itself converted to the corresponding amine is discussed.
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Doi:10.1246/cl.1978.649
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