Journal of the Chemical Society. Perkin transactions I p. 3165 - 3171 (1991)
Update date:2022-07-30
Topics:
Praly-Deprez, Isabelle
Rivalle, Christian
Huel, Christiane
Belehradek, Jean
Paoletti, Claude
Bisagni, Emile
A route to 11-amino-substituted-6H-pyrido<4,3-b>carbazoles has been studied.Thus, condensation of 2-(4-lithiopyridine-3-yl)-4,4-dimethyloxazoline with 2-acetyl-5-methoxy-1-phenylsulphonylindole led to a low yield of the expected alcohol, which upon hydrolysis gave a complex mixture.A better starting building block was 4-acetyl-N,N-diisopropylnicotinamide obtained either from N,N-diisopropyl-4-lithionicotinamide (low yield) or from pyridine-3,4-dicarboxylic anhydride, using a 4-step sequence.This compound was treated with 2-lithio-5-methoxy-1-phenylsulphonylindole, affording N,N-diisopropyl-4-<1-(5-methoxy-1-phenylsulphonylindol-2-yl)-1- hydroxyethyl>nicotinamide.Hydrolysis and then reduction led to 4-<1-(5-methoxy-1-phenylsulphonylindol-2-yl)ethyl>nicotinic acid whose amides were cyclized by phosphorus trichlorideoxide.Finally, the title compounds were obtained by Raney-nickel reduction-elimination of the 6-phenylsulphonyl protecting group.
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