Premium
The synthesis of 5‐azaindoles by substitution‐rearrangement of 7‐azaindoles upon treatment with certain primary amines
Author(s) -
Girgis Nabih S.,
Larson Steven B.,
Robins Roland K.,
Cottam Howard B.
Publication year - 1989
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.5570260210
Subject(s) - chemistry , yield (engineering) , nucleophilic substitution , primary (astronomy) , substitution (logic) , nucleophilic aromatic substitution , substitution reaction , medicinal chemistry , stereochemistry , materials science , physics , astronomy , computer science , metallurgy , programming language
Certain 4‐substituted 1 H ‐pyrrolo[2,3‐ b ]pyridines (7‐azaindoles) undergo a nucleophilic substitution‐rearrangement upon treatment with various primary amines at elevated temperatures to yield N ‐1‐substituted 4‐amino‐1 H ‐pyrrolo[3,2‐ c ]pyridines (5‐azaindoles). Treatment of the same 7‐azaindoles with secondary amines under the same reaction conditions led to simple nucleophilic substitution products.