Research

Chemical Sciences

Title :

Harnessing Anthranil as a Nitrene Precursor for Intramolecular C-H Amination: A Modular Approach for the Synthesis of Nitrogen Heterocycles

Area of research :

Chemical Sciences

Principal Investigator :

Dr. Amit Balkrishna Pawar, Indian Institute Of Technology (IIT) Mandi, Himachal Pradesh

Timeline Start Year :

2024

Timeline End Year :

2027

Contact info :

Equipments :

Details

Executive Summary :

Nitrene is one of the important reactive intermediates in organic synthesis. Moreover, intramolecular nitrene insertion has been an instrumental strategy for accessing a diverse range of biologically active heterocyclic scaffolds such as indoles, carbazoles, pyrroles, etc. The recent development in the area of intramolecular nitrene insertion led to the discovery of various organic molecules which can serve as a nitrene precursor. It includes iminoiodinanes, azides, N-tosyloxycarbamates, and dioxazolones. However, the utilization of anthranil as a nitrene precursor for intramolecular C-H amination is very rare in the literature. This project aims to develop a modular strategy for utilizing anthranil as a nitrene precursor for synthesizing various biologically important N-heterocyles such as carbazoles, indoles, phenoxazines, dihydrophenazines, phenothiazines, indolines, and 1,3-azoles via intramolecular C-H amination utilizing first-row transition metal catalysts such as Cobalt and Iron due to its cost-effectiveness. The intramolecular C-H amination reactions will be attempted at sp² C-H as well as chemically inert sp³ C-H bonds. As a proof of concept, we have incorporated our initial results pertaining to this project under the section "work plan."

Total Budget (INR):

57,14,500

Organizations involved