Ethyl 2-chlorooxazole-4-carboxylate: a versatile intermediate for the synthesis of substituted oxazoles.
@article{Hodgetts2002Ethyl2A, title={Ethyl 2-chlorooxazole-4-carboxylate: a versatile intermediate for the synthesis of substituted oxazoles.}, author={K. Hodgetts and Mark T. Kershaw}, journal={Organic letters}, year={2002}, volume={4 17}, pages={ 2905-7 } }
[reaction: see text] By using a sequence of regiocontrolled halogenation and palladium-catalyzed coupling reactions, the synthesis of variously substituted oxazoles from ethyl 2-chlorooxazole-4-carboxylate (2) was accomplished. The methodology was applied to the synthesis of a series of 2,4-disubstituted, 2,5-disubstituted, and 2,4,5-trisubstituted oxazoles.
Topics from this paper
41 Citations
4-Bromomethyl-2-chlorooxazole––a versatile oxazole cross-coupling unit for the synthesis of 2,4-disubstituted oxazoles
- Chemistry
- 2004
- 27
Synthesis of 2-(hetero)aryl-5-(trimethylsilylethynyl)oxazoles from (hetero)arylacrylic acids.
- Chemistry, Medicine
- Organic letters
- 2015
- 11
Derivatization of a tris-oxazole using Pd-catalyzed coupling reactions of a 5-bromooxazole moiety
- Chemistry
- 2010
- 17
Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid
- Chemistry, Medicine
- Beilstein journal of organic chemistry
- 2017
- 3
- PDF
References
SHOWING 1-10 OF 33 REFERENCES
Dimethyl amino[(phenylthio)methyl]malonate: a useful C-3 unit in a mild, direct synthesis of oxazole-4-carboxylates
- Chemistry
- 1993
- 22
Rhodium-catalyzed heterocycloaddition route to 1,3-oxazoles as building blocks in natural products synthesis
- Chemistry
- 1993
- 37
Palladium-Catalyzed Reactions of Terminal Acetylenes and Olefins with Halo-1, 3-azoles
- Chemistry
- 1987
- 28
- PDF
A new method for the formation of 2,4-disubstituted oxazoles: internal transfer of oxidation state through a molecular framework
- Chemistry
- 2000
- 13
A synthetic approach towards the aromatic macrocyclic core of diazonamide A based on sp2-sp2 coupling protocols
- Chemistry
- 1998
- 26
Palladium-catalyzed cross-coupling of terminal alkynes with 4-trifloyloxazole: studies toward the construction of the C26-C31 subunit of phorboxazole A.
- Chemistry, Medicine
- Organic letters
- 2000
- 40