Unusual ring transformation of 2-halogeno-N-phenacylpyridinium salts in reaction with secondary amines: a facile 'one-pot' route to 1-amino-4-(oxazol-2-yl)butadienes

Authors
Babaev, EV Tsisevich, AA
Citation
Ev. Babaev et Aa. Tsisevich, Unusual ring transformation of 2-halogeno-N-phenacylpyridinium salts in reaction with secondary amines: a facile 'one-pot' route to 1-amino-4-(oxazol-2-yl)butadienes, J CHEM S P1, (4), 1999, pp. 399-401
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
4
Year of publication
1999
Pages
399 - 401
Database
ISI
SICI code
0300-922X(19990221):4<399:URTO2S>2.0.ZU;2-G
Abstract
2-Halogeno-N-phenacylpyridinium,salts 1 (Hal = Cl, Ar = p-NO2Ph; Hal = Br, Ar =Ph) in reaction with aliphatic secondary amines undergo an unusual ring transformation to 1-amino-4-(5-aryloxazol-2-yl)buta-1,3-dienes 9 and 10. T he configuration of the products (1E,3E or 1E,3Z) depends on the reaction t emperature A suggested mechanism for the transformation involves intermedia te formation of 2-aryloxazolo[3,2-a]pyridinium salt 4.