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Literature DB >> 22394197

Palladium-catalyzed N-arylation of 2-aminothiazoles.

Meredeth A McGowan¹, Jaclyn L Henderson, Stephen L Buchwald.

Abstract

A method for the Pd-catalyzed coupling of 2-aminothiazole derivatives with aryl bromides and triflates is described. Significantly, for this class of nucleophiles, the coupling exhibits a broad substrate scope and proceeds with a reasonable catalyst loading. Furthermore, an interesting effect of acetic acid as an additive is uncovered that facilitates catalyst activation.

Entities: Chemical Disease Gene

Mesh：

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Year: 2012 PMID： 22394197 PMCID： PMC3319723 DOI： 10.1021/ol300178j

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

19 in total

Review 1. Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective.

Authors: Eric Assen B Kantchev; Christopher J O'Brien; Michael G Organ
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. Aminothiazoles as γ-secretase modulators.

Authors: Thomas Lübbers; Alexander Flohr; Synese Jolidon; Pascale David-Pierson; Helmut Jacobsen; Laurence Ozmen; Karlheinz Baumann
Journal: Bioorg Med Chem Lett Date: 2011-08-19 Impact factor: 2.823

3. Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles.

Authors: Satoshi Ueda; Mingjuan Su; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2011-08-18 Impact factor: 15.336

4. 2-aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1- piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor.

Authors: Jagabandhu Das; Ping Chen; Derek Norris; Ramesh Padmanabha; James Lin; Robert V Moquin; Zhongqi Shen; Lynda S Cook; Arthur M Doweyko; Sidney Pitt; Suhong Pang; Ding Ren Shen; Qiong Fang; Henry F de Fex; Kim W McIntyre; David J Shuster; Kathleen M Gillooly; Kamelia Behnia; Gary L Schieven; John Wityak; Joel C Barrish
Journal: J Med Chem Date: 2006-11-16 Impact factor: 7.446

5. Modulation of gamma-secretase reduces beta-amyloid deposition in a transgenic mouse model of Alzheimer's disease.

Authors: Maria Z Kounnas; Anne M Danks; Soan Cheng; Curtis Tyree; Elizabeth Ackerman; Xulun Zhang; Kwangwook Ahn; Phuong Nguyen; Dan Comer; Long Mao; Chengzhi Yu; David Pleynet; Paul J Digregorio; Gonul Velicelebi; Kenneth A Stauderman; William T Comer; William C Mobley; Yue-Ming Li; Sangram S Sisodia; Rudolph E Tanzi; Steven L Wagner
Journal: Neuron Date: 2010-09-09 Impact factor: 17.173

Palladium-catalyzed N-arylation of 2-aminothiazoles.

Review 1. Palladium complexes of N-heterocyclic carbenes as catalysts for cross-coupling reactions--a synthetic chemist's perspective.

2. Aminothiazoles as γ-secretase modulators.

3. Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles.

5. Modulation of gamma-secretase reduces beta-amyloid deposition in a transgenic mouse model of Alzheimer's disease.

Review 6. Biaryl phosphane ligands in palladium-catalyzed amination.

7. Pd-catalyzed N-arylation of heteroarylamines.

8. An Efficient System For the Pd-Catalyzed Cross-Coupling of Amides and Aryl Chlorides.

9. Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

10. Discovery of 2-aminothiazoles as potent antiprion compounds.

1. Palladium-catalyzed N-monoarylation of amidines and a one-pot synthesis of quinazoline derivatives.

2. Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

3. Catalyst-controlled chemoselective arylation of 2-aminobenzimidazoles.

4. 2-Aminooxazole as a Novel Privileged Scaffold in Antitubercular Medicinal Chemistry.

Review 5. Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

6. Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.