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Intramolecular Inverse Electron-Demand [4 + 2] Cycloadditions of Ynamides with Pyrimidines: Scope and Density Functional Theory Insights

Duret, Guillaume and Quinlan, Robert and Yin, Boyang and Martin, Rainer E. and Bisseret, Philippe and Neuburger, Markus and Gandon, Vincent and Blanchard, Nicolas. (2017) Intramolecular Inverse Electron-Demand [4 + 2] Cycloadditions of Ynamides with Pyrimidines: Scope and Density Functional Theory Insights. Journal of Organic Chemistry, 82 (3). pp. 1726-1742.

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Official URL: http://edoc.unibas.ch/59102/

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Abstract

4-Aminopyridines are valuable scaffolds for the chemical industry in general, from life sciences to catalysis. We report herein a collection of structurally diverse polycyclic fused and spiro-4-aminopyridines that are prepared in only three steps from commercially available pyrimidines. The key step of this short sequence is a [4 + 2]/ retro -[4 + 2] cycloaddition between a pyrimidine and an ynamide, which constitutes the first examples of ynamides behaving as electron-rich dienophiles in [4 + 2] cycloaddition reactions. In addition, running the ih DA/ r DA reaction in continuous mode in superheated toluene, to overcome the limited scalability of MW reactions, results in a notable production increase compared to batch mode. Finally, density functional theory investigations shed light on the energetic and geometric requirements of the different steps of the ih DA/ r DA sequence.
Faculties and Departments:05 Faculty of Science > Departement Chemie
UniBasel Contributors:Neuburger, Markus
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:0022-3263
e-ISSN:1520-6904
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:24 Jan 2018 11:12
Deposited On:24 Jan 2018 11:12

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