Visible Light Induced Catalyst-free Deaminative C-2 Alkylation of Heterocyclic-N-Oxides using Katritzky salts.

17 February 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

HEREIN, AN UNPRECEDENTED DIRECT C-2 ALKYLATION OF QUINOLINE-N-OXIDES WITH KATRITZKY SALTS VIA VISIBLE-LIGHT INDUCED CATALYST-FREE DEAMINATIVE APPROACH WAS DEVELOPED. MECHANISTIC STUDIES REVEALED THAT KATRITZKY SALTS AND BASE WERE INVOLVED TO GENERATE AN EDA COMPLEX, WHICH UNDERWENT INTERMOLECULAR SINGLE ELECTRON TRANSFER (SET) TO GIVE ALKYL RADICAL INTERMEDIATE. FINALLY, ALKYL RADICAL INTERMEDIATE FURTHER UNDERWENT-ADDITION WITH QUINOLINE-N-OXIDE SUBSTRATES TO ACCESS THE DESIRED ADDUCTS IN EXCELLENT YIELD.

Supplementary materials

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Description
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Title
Visible Light Induced Catalyst-free Deaminative C-2 Alkylation of Heterocyclic-N-Oxides using Katritzky salts.
Description
N-heteroaromatic compounds play a vital role in nature and medicine.1 Among them, quinolines and its functionalized derivatives represent a key component in a variety of biologically active moieties and drug molecules such as quinine, Montelucast, Mefloquine, Vacquinol-1, etc.2 Because of the poor selectivity and reactivity associated with the low-energy -system, direct C-2 functionalization of quinolines is a major challenge in synthetic organic chemistry. To address this problem, the utilization of easily accessible quinoline-N-oxides is an alternate approach where O-directed functionalization of these scaffolds results in excellent regioselectivity. we have demonstrated a mild and efficient EDA driven, visible-light enabled strategy for the synthesis of C-2 alkylated heterocyclic-N-oxides via catalyst-free deamination of Katritzky salts with quinoline-N-oxides. The method provides a mild access to a series of C-2 alkylated quinoline-N-oxide, quinoxaline-N-oxide and pyridine-N-oxide derivatives. Moreover, a series of control experiments elucidated the reaction mechanism.
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