Introduction of substituents in the pyridine proton of 7-azaindoline
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Electropilic substitution (nitration, bromination, and chlorination) of 4-methyl-6-chloro-7-azaindoline (and its N-acetyl derivative) takes place in the 5 position. 4-Methyl-5-amino-7-azaindoline, 4-methyl-5-nitro-7-azaindoline, and 1-acetyl-4-methyl-5-amino-6-chloro-7-azaindoline were obtained by reduction of 1-acetyl-4-methyl-5-nitro-6-chloro-7-azaindoline under various conditions. A method was developed for the preparation of a new three-ring system — 1,2,3-oxadiazolo[5,4-b]-pyrrolo[2,3-e]pyridine.
KeywordsOrganic Chemistry Pyridine Nitration Pyridine Proton
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