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Literature DB >> 22838632

Room temperature copper(II)-catalyzed oxidative cyclization of enamides to 2,5-disubstituted oxazoles via vinylic C-H functionalization.

Abstract

A copper(II)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.

Entities: Chemical Disease Species

Mesh：

Substances：
Amides
Oxazoles
Copper

Year: 2012 PMID： 22838632 PMCID： PMC3454444 DOI： 10.1021/jo301332s

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

53 in total

Review 1. Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant.

Authors: Zhuangzhi Shi; Chun Zhang; Conghui Tang; Ning Jiao
Journal: Chem Soc Rev Date: 2012-02-22 Impact factor: 54.564

2. Synthesis of secondary enamides by ruthenium-catalyzed selective addition of amides to terminal alkynes.

Authors: Lukas J Goossen; Kifah S M Salih; Mathieu Blanchot
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Rh(III)-catalyzed oxidative olefination of vinylic C-H bonds: efficient and selective access to di-unsaturated α-amino acid derivatives and other linear 1,3-butadienes.

Authors: Tatiana Besset; Nadine Kuhl; Frederic W Patureau; Frank Glorius
Journal: Chemistry Date: 2011-05-25 Impact factor: 5.236

4. An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation.

Authors: Weimin He; Chaoqun Li; Liming Zhang
Journal: J Am Chem Soc Date: 2011-05-12 Impact factor: 15.419

5. Expedient synthesis of N-acyl anthranilamides and β-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C-H bonds with isocyanates.

Authors: Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2011-07-08 Impact factor: 15.419

6. Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation.

Authors: Murali Mohan Guru; Md Ashif Ali; Tharmalingam Punniyamurthy
Journal: J Org Chem Date: 2011-06-02 Impact factor: 4.354

7. Characterization of novel diaryl oxazole-based compounds as potential agents to treat pancreatic cancer.

Authors: Arthur Y Shaw; Meredith C Henderson; Gary Flynn; Betty Samulitis; Haiyong Han; Steve P Stratton; H-H Sherry Chow; Laurence H Hurley; Robert T Dorr
Journal: J Pharmacol Exp Ther Date: 2009-08-05 Impact factor: 4.030

8. The chemistry of Pseudomonic acid. 15. Synthesis and antibacterial activity of a series of 5-alkyl, 5-alkenyl, and 5-heterosubstituted oxazoles.

Authors: P Brown; D T Davies; P J O'Hanlon; J M Wilson
Journal: J Med Chem Date: 1996-01-19 Impact factor: 7.446

3. Gold-catalyzed tandem reactions of amide-aldehyde-alkyne coupling and cyclization-synthesis of 2,4,5-trisubstituted oxazoles.

Authors: Pierre Querard; Simon A Girard; Nick Uhlig; Chao-Jun Li
Journal: Chem Sci Date: 2015-10-06 Impact factor: 9.825

3 in total