Photocatalytic, a-Aminoalkyl Radical-Mediated, Methylene-Extrusive Ring-Closing Transformation of o-Alkynyl and o-Cyano Acrylamides

Autor: Upreti, Ganesh Chandra, Singh, Tavinder, Khanna, Kirti, Sahoo, Debasish, Singh, Anand
Zdroj: Organic Letters; May 2024, Vol. 26 Issue: 17 p3652-3656, 5p
Abstrakt: Herein we report a visible-light-induced, a-aminoalkyl radical-mediated cascade reaction of 1,7-enynes that establishes a unique ring-closing enyne transformation pathway which occurs with concomitant loss of a methylene moiety. The a-aminoalkyl radical derived from N,N-dimethylaniline was demonstrated to be a traceless promoter of enyne reorganization leading to 4-alkylquinolinones. The reaction can also be extended to nitrile-substituted acrylamide systems, leading to carbostyrils. Experiments with deuterated N,N-dimethylaniline-d6(PhN(CD3)2) established the involvement of 1,5-H atom transfer in the mechanism.
Databáze: Supplemental Index