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The reaction of 3‐hydroxypyridine N ‐oxide with active hydrogen compounds and the synthesis of 3‐substituted 2‐aminofuro[3,2‐ b ] pyridines
Author(s) -
Stein M. Luisa,
Manna Fedele,
Lombardi Carmine C.
Publication year - 1978
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.5570150833
Subject(s) - chemistry , malononitrile , tautomer , acetic anhydride , oxide , medicinal chemistry , ethyl cyanoacetate , organic chemistry , hydrogen , catalysis
3‐Hydroxypyridine N ‐oxide reacts readily in acetic anhydride with ethyl cyanoacetate, cyanoacetone and malononitrile. The three reaction products (2‐substituted‐3‐acetoxypyridines) show different equilibria between tautomeric structures; in strong acids they undergo cyclization to 3‐substituted 2‐aminofuro[3,2‐ b ]pyridines.