A Direct Synthesis of Oxazoles from Aldehydes
- 19 July 2010
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (16), 3614-3617
- https://doi.org/10.1021/ol101346w
Abstract
An expedient method for the direct conversion of aldehydes to 2,4-disubstituted oxazoles is presented. The method relies on the oxidation of an oxazolidine formed from the condensation of serine with an aldehyde and proceeds through a 2,5-dihydrooxazole intermediate. In contrast to standard methods that start from carboxylic acids, the use of aldehydes as starting materials does not require intermediate purification and affords the oxazoles under relatively mild conditions.Keywords
This publication has 57 references indexed in Scilit:
- Timely synthetic support for medicinal chemistsDrug Discovery Today, 2005
- An Efficient, Practical Approach to the Synthesis of 2,4-Disubstituted Thiazoles and Oxazoles: Application to the Synthesis of GW475151Organic Process Research & Development, 2000
- Enantioselective Molybdenum-Catalyzed Allylic Alkylation Using Chiral Bisoxazoline LigandsOrganic Letters, 1999
- Tricyclic heteroaromatic systems. Synthesis and benzodiazepine receptor affinity of 2-substituted-1-benzopyrano[3,4-d]oxazol-4-ones, -thiazol-4-ones, and -imidazol-4-onesIl Farmaco, 1998
- Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-X Mode: Convenient Route to 3-OxazolinesThe Journal of Organic Chemistry, 1996
- Cupric bromide mediated oxidation of 4-carboxyoxazolines to the corresponding oxazolesThe Journal of Organic Chemistry, 1993
- The Atom Economy—A Search for Synthetic EfficiencyScience, 1991
- Nickel peroxide dehydrogenation of oxygen-, sulfur-, and nitrogen-containing heterocyclesThe Journal of Organic Chemistry, 1979
- Studies on Azole Compounds. III. Reactions of Oxazole N-Oxides with Phosphoryl Chloride and Acetic AnhydrideCHEMICAL & PHARMACEUTICAL BULLETIN, 1971
- The Synthesis of Imidazoles and Oxazoles from α-Diketone Monoximes1Journal of the American Chemical Society, 1955