Anthraquinone-photocatalysed addition of amines to α,β-unsaturated esters: a novel route to indolizidone, pyrrolizidone and related ring systems
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 14,p. 1797-1799
- https://doi.org/10.1039/p19950001797
Abstract
The indolizidone 9, the pyrrolizidone 14, a mixture of heliotridone 15a and pseudoheliotridone 15b and the lactam 19 have been synthesized in a one-step anthraquinone-photocatalysed reaction of the corresponding amines, piperidine 1, pyrrolidine 10 and morpholine 16, with α,β-unsaturated esters.Keywords
This publication has 18 references indexed in Scilit:
- Photocatalyzed multiple additions of amines to .alpha.,.beta.-unsaturated esters and nitrilesThe Journal of Organic Chemistry, 1994
- Mechanistic and synthetic aspects of amine-enone single electron transfer photochemistryAccounts of Chemical Research, 1992
- Radical cyclization reactions of .alpha.-silyl amine .alpha.,.beta.-unsaturated ketone and ester systems promoted by single electron transfer photosensitizationJournal of the American Chemical Society, 1991
- A new alkylation method of the carbon α to the nitrogen of secondary aminesTetrahedron Letters, 1991
- A novel and selective procedure for generating iminium cation by photosensitized (set) oxidative reactionTetrahedron Letters, 1988
- Metalation and electrophilic substitution of amine derivatives adjacent to nitrogen: .alpha.-metallo amine synthetic equivalentsChemical Reviews, 1984
- Tetrahydropyridones via intramolecular ureidomercurationTetrahedron Letters, 1983
- New methods for alkaloid synthesis: .alpha.-acylamino radical cyclizationsJournal of the American Chemical Society, 1982
- Solvent effects on the picosecond dynamics of the photoreduction of benzophenone by aromatic aminesJournal of the American Chemical Society, 1981
- PHOTOCHEMISTRY OF ANTHRAQUINONE‐2,6‐DISODIUM SULPHONATE IN AQUEOUS SOLUTIONPhotochemistry and Photobiology, 1981