Issue 12, 1991

Synthesis of 11-amino-substituted-9-methoxy-5-methyl-6H-pyrido[4,3-b]-carbazoles

Abstract

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1991, 3165-3171

Synthesis of 11-amino-substituted-9-methoxy-5-methyl-6H-pyrido[4,3-b]-carbazoles

I. Praly-Deprez, C. Rivalle, C. Huel, J. Belehradek, C. Paoletti and E. Bisagni, J. Chem. Soc., Perkin Trans. 1, 1991, 3165 DOI: 10.1039/P19910003165

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