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Literature DB >> 20718452

Lewis acid catalyzed inverse electron-demand Diels-Alder reaction of 1,2-diazines.

Abstract

A systematic approach toward Lewis acid catalyzed inverse electron-demand Diels-Alder (IEDDA) reactions of 1,2-diazines is described. The general concept is first investigated by DFT calculations, supported by spectroscopic data, and finally proven in the experiment.

Entities: Chemical

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Year: 2010 PMID： 20718452 DOI： 10.1021/ol101701z

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

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Cited

16 in total

1. Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.

Authors: Christopher M Glinkerman; Dale L Boger
Journal: Org Lett Date: 2018-04-16 Impact factor: 6.005

2. Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

Authors: Christopher M Glinkerman; Dale L Boger
Journal: Org Lett Date: 2015-07-14 Impact factor: 6.005

3. Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope.

Authors: Erin D Anderson; Dale L Boger
Journal: J Am Chem Soc Date: 2011-07-19 Impact factor: 15.419

8. Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin.

Authors: Christopher M Glinkerman; Dale L Boger
Journal: J Am Chem Soc Date: 2016-09-14 Impact factor: 15.419

9. Synthesis, Characterization, and Cycloaddition Reactivity of a Monocyclic Aromatic 1,2,3,5-Tetrazine.

Authors: Zhi-Chen Wu; Dale L Boger
Journal: J Am Chem Soc Date: 2019-10-02 Impact factor: 15.419

10. Pyridazine N-Oxides as Precursors to 2-Aminofurans: Scope and Limitations in Complexity Building Cascade Reactions.

Authors: Maribel Borger; James H Frederich
Journal: Org Lett Date: 2019-03-22 Impact factor: 6.072

Lewis acid catalyzed inverse electron-demand Diels-Alder reaction of 1,2-diazines.

1. Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.

2. Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

3. Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope.

4. Scope of the inverse electron demand Diels-Alder reactions of 1,2,3-triazine.

5. Silver-catalyzed formal inverse electron-demand Diels-Alder reaction of 1,2-diazines and siloxy alkynes.

6. Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.

7. Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding.

8. Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin.

9. Synthesis, Characterization, and Cycloaddition Reactivity of a Monocyclic Aromatic 1,2,3,5-Tetrazine.

10. Pyridazine N-Oxides as Precursors to 2-Aminofurans: Scope and Limitations in Complexity Building Cascade Reactions.