Construction of tetrahydrobenzo[f]quinoline scaffolds via polar [4 + 2]-Cycloaddition reaction with arynes as dienophiles. (6th July 2022)

• Record Type: Journal Article
• Authors: Pandya, Virat G.; Mhaske, Santosh B.
• Is Part Of: Tetrahedron letters. Volume 101(2022)
• Publication Date: 2022-07-06
• Subjects: Aryne -- Diene -- Diels-Alder -- Tetrahydrobenzo[f]quinoline; DME Dimethoxyethane -- TBAF Tetra-n-butylammonium fluoride -- TBAT Tetrabutylammonium difluorotriphenylsilicate -- THF Tetrahydrofurane -- ACN Acetonitrile -- KF potassium fluoride; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153901
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A transition-metal-free route has been developed for the direct synthesis of biologically significant tetrahydrobenzo[ f ]quinoline scaffolds. The reaction features polar [4 + 2] Diels-Alder cycloaddition reaction of arynes with a well-designed diene N -Boc protected vinyl tetrahydropyridine, followed by the isomerisation of the double bond leading to the formation of tetrahydrobenzo[ f ]quinoline scaffolds in good to moderate yields.