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Alcohols and aluminium alkoxides in the presence of raney nickel as alkylating agents. 1. Alkylation of indoles and pyrroles
Author(s) -
Botta M.,
De Angelis F.,
Nicoletti R.
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160318
Subject(s) - chemistry , alkylation , reagent , raney nickel , alkyl , aluminium , indole test , nickel , organic chemistry , medicinal chemistry , substrate (aquarium) , catalysis , oceanography , geology
Indole and 3‐methylindole are completely converted by alcohols into N ‐alkyl or N ‐isoalkyl derivatives in the presence of aluminium alkoxides and Raney Nickel; 2‐methylindole gives lower yields. Pyrroles suffer N ‐ and C ‐alkylation but the initially formed N ‐alkylpyrroles are reduced into N ‐alkylpyrrolidines in the reaction mixtures. The occurrence of these N ‐alkylations is at variance with the C‐alkylation of indoles and pyrroles which takes place by means of alcohols and sodium alkoxides. This suggests that the reaction occurs between the substrate and the reagent both coordinated by aluminium.