(Chemical Equation Presented) Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.
Intramolecular Pd(II)-Catalyzed Cyclization of Propargylamides : Straightforward Synthesis of 5-Oxazolecarbaldehydes / E. Beccalli, E. Borsini, G. Broggini, G. Palmisano, S. Sottocornola. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 73:12(2008), pp. 4746-4749. [10.1021/jo800621n]
Intramolecular Pd(II)-Catalyzed Cyclization of Propargylamides : Straightforward Synthesis of 5-Oxazolecarbaldehydes
E. BeccalliPrimo
;
2008
Abstract
(Chemical Equation Presented) Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.Pubblicazioni consigliate
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