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

Almerico A. M. | Zendy; Cirrincione G. | Zendy; Diana P. | Zendy; Grimaudo S. | Zendy; Dattolo G. | Zendy; Aiello E. | Zendy; Mingoia F. | Zendy

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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 .

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