The synthesis of 5‐azaindoles by substitution‐rearrangement of 7‐azaindoles upon treatment with certain primary amines | Zendy

Girgis Nabih S. | Zendy; Larson Steven B. | Zendy; Robins Roland K. | Zendy; Cottam Howard B. | Zendy

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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.

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