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Literature DB >> 15704932

Oxaziridine-mediated amination of primary amines: scope and application to a one-pot pyrazole synthesis.

Alan Armstrong¹, Lyn H Jones, Jamie D Knight, Richard D Kelsey.

Abstract

Electrophilic amination of primary aliphatic and aromatic amines is reported using a diethylketomalonate-derived oxaziridine to afford the corresponding N-Boc hydrazines in good to excellent yields. The method allows a one-pot synthesis of pyrazoles from primary amines. [Reaction: see text]

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 15704932 DOI： 10.1021/ol0474507

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

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Cited

7 in total

1. Palladium-Catalyzed Pyrazole-Directed sp³ C-H Bond Arylation for the Synthesis of β-Phenethylamines.

Authors: Nurbey Gulia; Olafs Daugulis
Journal: Angew Chem Int Ed Engl Date: 2017-02-24 Impact factor: 15.336

2. Synthesis and evaluation of vancomycin aglycon analogues that bear modifications in the N-terminal D-leucyl amino acid.

Authors: Christine M Crane; Dale L Boger
Journal: J Med Chem Date: 2009-03-12 Impact factor: 7.446

Review 3. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors: Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal: Chem Soc Rev Date: 2018-08-28 Impact factor: 54.564

4. P^III/P^V═O-Catalyzed Intermolecular N-N Bond Formation: Cross-Selective Reductive Coupling of Nitroarenes and Anilines.

Authors: Gen Li; Steven P Miller; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2021-09-02 Impact factor: 16.383

Oxaziridine-mediated amination of primary amines: scope and application to a one-pot pyrazole synthesis.

1. Palladium-Catalyzed Pyrazole-Directed sp³ C-H Bond Arylation for the Synthesis of β-Phenethylamines.

2. Synthesis and evaluation of vancomycin aglycon analogues that bear modifications in the N-terminal D-leucyl amino acid.

Review 3. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

4. P^III/P^V═O-Catalyzed Intermolecular N-N Bond Formation: Cross-Selective Reductive Coupling of Nitroarenes and Anilines.

5. N-Amino peptide scanning reveals inhibitors of Aβ₄₂ aggregation.

6. Advances in the chemistry of oxaziridines.

Review 7. Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines.

Oxaziridine-mediated amination of primary amines: scope and application to a one-pot pyrazole synthesis.

1. Palladium-Catalyzed Pyrazole-Directed sp3 C-H Bond Arylation for the Synthesis of β-Phenethylamines.

2. Synthesis and evaluation of vancomycin aglycon analogues that bear modifications in the N-terminal D-leucyl amino acid.

Review 3. A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

4. PIII/PV═O-Catalyzed Intermolecular N-N Bond Formation: Cross-Selective Reductive Coupling of Nitroarenes and Anilines.

5. N-Amino peptide scanning reveals inhibitors of Aβ42 aggregation.

6. Advances in the chemistry of oxaziridines.

Review 7. Recent Advances in the Catalytic Asymmetric Reactions of Oxaziridines.

1. Palladium-Catalyzed Pyrazole-Directed sp³ C-H Bond Arylation for the Synthesis of β-Phenethylamines.

4. P^III/P^V═O-Catalyzed Intermolecular N-N Bond Formation: Cross-Selective Reductive Coupling of Nitroarenes and Anilines.

5. N-Amino peptide scanning reveals inhibitors of Aβ₄₂ aggregation.