Reaction of amino substituted heterocycles with one heteroatom in a five-membered ring as enamines. A revision

Autor:	Francesco Mingoia, Patrizia Diana, Gaetano Dattolo, Stefania Grimaudo, Anna Maria Almerico, Enrico Aiello, Girolamo Cirrincione
Rok vydání:	1995
Předmět:	chemistry.chemical_compound chemistry Furan Organic Chemistry Heteroatom Electrophile Thiophene chemistry.chemical_element Protonation Ring (chemistry) Nitrogen Medicinal chemistry Pyrrole
Zdroj:	Journal of Heterocyclic Chemistry. 32:985-989
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570320352
Popis:	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.
Databáze:	OpenAIRE
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