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Furopyridines. XIX . Reaction of furo[2,3‐ b ]‐, ‐[3,2‐ b ]‐, ‐[2,3‐ c ]‐ and ‐[3,2‐ c ]pyridine with acetic anhydride
Author(s) -
Shiotani Shunsaku,
Taniguchi Katsunori,
Ishida Toshimasa,
In Yasuko
Publication year - 1996
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.5570330321
Subject(s) - chemistry , acetic anhydride , pyridine , furan , ring (chemistry) , mass spectrum , medicinal chemistry , nitrogen , stereochemistry , mass spectrometry , organic chemistry , catalysis , chromatography
Acetoxylation of N ‐oxide of furo[2,3‐ b ]‐ 2a , ‐[3,2‐ b ]‐ 2b , ‐[2,3‐ c ]‐ 2c and ‐[3,2‐ c ]pyridine 2d with acetic anhydride afforded compounds substituted normally at the α‐ or γ‐position to the ring nitrogen, 3a, 4a, 4b, 3d, 4d, 8 and 9 , and in addition compounds substituted on the furan ring, 5a, 6a, 5b, 6b, 7b, 5c and 7c which were unexpected compounds. The structures of these compounds were established from the ir, nmr and mass spectra, and x‐ray crystal analysis of 5b .