Iron dichloride induced isomerization or reductive cleavage of isoxazoles: A facile synthesis of 2-carboxy-azirines
5-Alkoxy-isoxazoles and N,N-disubstituted-5-isoxazolamines were found to isomerize to azirine derivatives by the use of iron dichloride as catalyst. On the contrary 5-alkyl- and 5-aryl-isoxazoles in the presence of the same salt, undergo reductive cleavage to enaminoketones. A common reaction intermediate is proposed.
Auricchio, Sergio,Bini, Antonella,Pastormerlo, Eros,Truscello, Ada M.
p. 10911 - 10920
(2007/10/03)
Cycloadditions, 18: 5-Aminoisoxazoles by Cycloaddition of Nitrile Oxides to Ynamines
Ten differently substituted ynamines 1a-j react with five nitrile oxides 3a-e to give the 5-aminoisoxazoles 4a-z.The stannyl-substituted ynamine 1k furnishes the same compounds (e.g. 4a-d) by reaction with the hydroximoyl chlorides 2a-d.Two representatives of 4 - b and p - can be transformed into the corresponding 1-azirine-3-carboxamides 6a and b.
Himbert, Gerhard,Kuhn, Hildegard,Barz, Michael
p. 403 - 407
(2007/10/02)
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