Premium
Synthesis of Quinazolinones, Imidazo[1,2‐ c ]quinazolines and Imidazo[4,5‐ c ]quinolines through Tandem Reductive Amination of Aryl Halides and Oxidative Amination of C(sp 3 )–H Bonds
Author(s) -
Nandwaitesh Kumar,
Dhiman Shiv,
Saini Hitesh Kumar,
Kumar Indresh,
Kumar Anil
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601329
Subject(s) - chemistry , amination , tandem , reductive amination , sodium azide , combinatorial chemistry , halide , aryl , aryl halide , azide , dimethylacetamide , oxidative phosphorylation , organic chemistry , medicinal chemistry , catalysis , alkyl , materials science , solvent , composite material , biochemistry
A tandem multicomponent approach has been described for the synthesis of quinazolinones, imidazo[1,2‐ c ]quinazolines and imidazo[4,5‐ c ]quinolines. The reaction involves a copper‐catalyzed reductive amination through azidation followed by reduction and oxidative amination of C(sp 3 )–H bonds of N , N ‐dimethylacetamide in the presence of TBHP ( tert ‐butylhydroperoxide) as oxidant. The method uses the easily available sodium azide as a nitrogen source and DMA ( N , N ‐dimethylacetamide) as a one‐carbon source for the synthesis of these N ‐fused heterocycles in good to excellent yields. The reaction can also be used for gram‐scale synthesis.