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The synthesis of various chloroimidazo[4,5‐c]pyridines and related derivatives
Author(s) -
Rousseau Robert J.,
Robins Roland K.
Publication year - 1965
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.5570020217
Subject(s) - chemistry , pyridine , triethyl orthoformate , acetic anhydride , ring (chemistry) , medicinal chemistry , closure (psychology) , organic chemistry , catalysis , economics , market economy
A new and convenient route to the synthesis of 4‐chloroimidazo[4,5‐c]pyridine (IV) has been devised. The preparation of 6‐chloroimidazo[4,5‐c]pyridine (IX) and 4,6‐dichloroimidazo[4, 5‐c]pyridine (XX) has been accomplished for the first time by ring closure of the requisite Chloro‐3.4‐diaminopyridines with ethyl orthoformate and acetic anhydride. Ring closure of 2,4,5‐triaminopyridine (XI) with ethyl orthoformate and acetic anhydride gave 6‐aminoimidazo[4, 5‐c]pyridine (XII). Imidazo[4, 5‐c]pyridine‐4‐thione (XXI has been prepared from 4‐chloroimidazo[4, 5‐c]pyridine.