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A study of 2‐aminofurans
Author(s) -
Lythgoe David J.,
Mcclenaghan Ian,
Ramsden Christopher A.
Publication year - 1993
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.5570300120
Subject(s) - chemistry , ring (chemistry) , pyridine , position (finance) , catalysis , product (mathematics) , medicinal chemistry , stereochemistry , organic chemistry , geometry , mathematics , finance , economics
Catalytic reduction of 2‐nitrofurans 2 gives low yields of 2‐aminofurans 1 which are not isolated but are trapped using ethyl ethoxymethylenecyanoacetate ( 6 ) or ethoxymethylenemalononitrile ( 7 ). In these reactions 2‐aminofuran ( 1a ) behaves like a dieneamine with substitution occurring at position 5 of the ring. When the 5‐position is substituted reaction takes place at position 3 and thermal cyclisation of the product gives furo‐[2,3‐ b ]pyridine derivatives 16 . An AM1 calculation of the properties of 2‐aminofuran ( 1a ) is reported and the results are consistent with observed properties.