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Studies on the chemical synthesis of potential antimetabolites. 30. Regioselective introduction of a chlorine atom into the imidazo[4,5‐ b ]pyridine nucleus
Author(s) -
Itoh Tokuo,
Ono Kazuo,
Sugawara Tomokazu,
Mizuno Yoshihisa
Publication year - 1982
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.5570190313
Subject(s) - chemistry , pyridine , regioselectivity , chlorine atom , nucleus , chloride , chlorine , phosphoryl chloride , medicinal chemistry , nucleoside , stereochemistry , organic chemistry , catalysis , biology , microbiology and biotechnology
Abstract Reactions of some imidazo[4,5‐ b ]pyridine 4‐oxides with phosphoryl chloride are described. Treatment of N ‐1‐substituted imidazo[4,5‐ b ]pyridine 4‐oxides with phosphoryl chloride led to the predominant formation of 7‐chloro derivatives. This feature was successfully applied to the preparation of a chloroimidazo[4,5‐ b ]pyridine nucleoside, which served as an important precursor of 1‐deazaadenosine.