Visible-light-induced organophotocatalytic and singlet oxygen-initiated domino construction of 1,4-dihydropyridines, C-3 functionalized spiro[indoline-3,4′-pyridines] and C-11 functionalized spiro[indeno-[1,2-b]quinoxaline-11,4′-pyridines]?

Organic & Biomolecular Chemistry Pub Date: 2023-01-17 DOI: 10.1039/D3OB00043E

Abstract

A highly efficient pot, atom, and step economical method for the construction of pharmacologically potent structurally functionalized 1,4-dihydropyridines, quaternary centered C-3 functionalized spiro[indoline-3,4′-pyridines], and C-11 functionalized spiro[indeno[1,2-b]quinoxaline-11,4′-pyridines] via rose bengal photoredox catalysis under blue LED irradiation in an aqueous medium at room temperature has been developed. The products were isolated in excellent yields within a short reaction time for a variety of functional groups under transition metal- and ligand-free energy-efficient conditions in a green solvent system with high reaction mass efficiency and process mass intensity, which are the key advantages of the current work.

Graphical abstract: Visible-light-induced organophotocatalytic and singlet oxygen-initiated domino construction of 1,4-dihydropyridines, C-3 functionalized spiro[indoline-3,4′-pyridines] and C-11 functionalized spiro[indeno-[1,2-b]quinoxaline-11,4′-pyridines]
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