THE REACTION-MECHANISM OF 1,3-DICARBONYL COMPOUNDS WITH TRIFLIC ANHYDRIDE - ANOMALOUS CYCLIZATION OF ETHYL ACETOACETATE TO FROM 3-ETHOXYCARBONYL-2,6-DIMETHYL-4-PYRONE

Authors
MARTINEZ AG FERNANDEZ AH VILCHEZ DM UBEDA AH HANACK M SUBRAMANIAN LR
Citation
Ag. Martinez et al., THE REACTION-MECHANISM OF 1,3-DICARBONYL COMPOUNDS WITH TRIFLIC ANHYDRIDE - ANOMALOUS CYCLIZATION OF ETHYL ACETOACETATE TO FROM 3-ETHOXYCARBONYL-2,6-DIMETHYL-4-PYRONE, Anales de quimica, 91(1-2), 1995, pp. 121-123
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Anales de quimica → ACNP
ISSN journal
11302283
Volume
91
Issue
1-2
Year of publication
1995
Pages
121 - 123
Database
ISI
SICI code
1130-2283(1995)91:1-2<121:TRO1CW>2.0.ZU;2-N
Abstract
The reaction of ethyl acetoacetate (1) with triflic anhydride (Tf(2)O) in excess, in the presence of nitriles (3) affords 3-ethoxycarbonyl-2 ,6-dimethyl-4-pyrone (10), instead of 5-ethoxycarbonyl-4,6-dimethyl-2- pyrone (5), which is the usual product formed in the cyclization of 1 catalyzed by protic or Lewis acids.