REACTION OF AMINO-SUBSTITUTED HETEROCYCLES WITH ONE HETEROATOM IN A 5-MEMBERED RING AS ENAMINES - A REVISION

Authors
ALMERICO AM CIRRINCIONE G DIANA P GRIMAUDO S DATTOLO G AIELLO E MINGOIA F
Citation
Am. Almerico et al., REACTION OF AMINO-SUBSTITUTED HETEROCYCLES WITH ONE HETEROATOM IN A 5-MEMBERED RING AS ENAMINES - A REVISION, Journal of heterocyclic chemistry, 32(3), 1995, pp. 985-989
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
32
Issue
3
Year of publication
1995
Pages
985 - 989
Database
ISI
SICI code
0022-152X(1995)32:3<985:ROAHWO>2.0.ZU;2-C
Abstract
2-Aminoheterocycles (pyrrole, furan, and thiophene) exist in solution in the amino form of type 1 and 5. They undergo protonation at the exo cyclic nitrogen in DMSO/TFA and protonation at position 5 in TFA. Howe ver when the electrophile is different from proton the 2-aminoheterocy les do not react as enamines (C-acylation is never observed), but thei r behavior is typical of aromatic amines, giving rise to N-acylated pr oduct of type 9.