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10.23.4.4.2.1.2 Giving C-Carbon 5H-Pyrido[3,2-b]indoles

DOI: 10.1055/sos-SD-110-01096

Joule, J. A.Science of Synthesis Knowledge Updates, (20182354.

There are few examples of manipulation of carbon substituents on 5H-pyrido[3,2-b]indoles. The manipulation of the cyano group in 5H-pyrido[3,2-b]indole-3-carbonitrile 1062 to produce amide and carboxylic acid groups is entirely unexceptional. Thus, partial hydrolysis using sodium hydroxide with hydrogen peroxide [note: N1-oxidation of 5H-pyrido[3,2-b]indole (4) requires much stronger conditions: hydrogen peroxide in acetic acid at 90°C][‌489‌] gives primary amide 1063, and complete hydrolysis produces the acid 1060 (Scheme 404).

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