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(sp3)–H Bonds. Issue 3 (30th December 2016)

• Record Type: Journal Article
• Authors: Nandwana, Nitesh Kumar; Dhiman, Shiv; Saini, Hitesh Kumar; Kumar, Indresh; Kumar, Anil
• Is Part Of: European journal of organic chemistry. Issue 3(2017)
• Page Start: 514
• Page End: 522
• Publication Date: 2016-12-30
• Subjects: Multicomponent reactions -- Fused‐ring systems -- Nitrogen heterocycles -- Synthetic methods -- Copper -- Homogeneous catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601329
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : The synthesis of quinazolinones, imidazo[1, 2‐ c ]quinazolines and imidazo[4, 5‐ c ]quinolones has been achieved through a multicomponent copper‐catalyzed reaction using easily available sodium azide as a nitrogen source, and DMA ( N, N ‐dimethylacetamide) as a one‐carbon source. N ‐Fused heterocycles were obtained in good to excellent yields, and the reaction is suitable for gram‐scale synthesis.