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Reaction of amino substituted heterocycles with one heteroatom in a five‐membered ring as enamines. A revision
Author(s) -
Almerico A. M.,
Cirrincione G.,
Diana P.,
Grimaudo S.,
Dattolo G.,
Aiello E.,
Mingoia F.
Publication year - 1995
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.5570320352
Subject(s) - chemistry , protonation , heteroatom , pyrrole , thiophene , electrophile , furan , ring (chemistry) , medicinal chemistry , enamine , acylation , friedel–crafts reaction , organic chemistry , catalysis , ion
2‐Aminoheterocycles (pyrrole, furan, and thiophene) exist in solution in the amino form of type 1 and 5 . They undergo protonation at the exocyclic nitrogen in DMSO/TFA and protonation at position 5 in TFA. However when the electrophile is different from proton the 2‐aminoheterocyles do not react as enamines ( C ‐acylation is never observed), but their behavior is typical of aromatic amines, giving rise to N ‐acylated product of type 9 .