Three-component synthesis of highly functionalized 5-acetyloxazoles.
By a flexible three-component synthesis, alkoxy-substituted enamides are easily available from lithiated alkoxyallenes, nitriles and carboxylic acids (see scheme). The treatment of these versatile intermediates with trifluoroacetic acid provided 5-acetyloxazoles in moderate to good yields. Different substituents are possible at C-2 and C-5 and the 5-acetyl group is a suitable handle for further synthetic transformations.
Lechel
Tilman
T
Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.
Lentz
Dieter
D
Reissig
Hans-Ulrich
HU
D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011090:Polyenes / Q000737:chemistry*
D010080:Oxazoles; D011090:Polyenes