Glucose as an Eco‐Friendly Reductant in a One‐Pot Synthesis of 2, 3‐Dihydroquinazolin‐4(1H)‐ones. Issue 41 (30th August 2020)

• Record Type: Journal Article
• Authors: dos Santos, Thiago; Grundke, Caroline; Lucas, Tobias; Großmann, Luca; Clososki, Giuliano Cesar; Opatz, Till
• Is Part Of: European journal of organic chemistry. Issue 41(2020)
• Page Start: 6429
• Page End: 6432
• Publication Date: 2020-08-30
• Subjects: Biomass -- Carbohydrates -- Dihydroquinazolinones -- One‐pot reactions -- Reduction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000970
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Carbohydrates such as glucose are an abundant renewable resource that can be employed in synthetic processes as a source of carbon and/or hydrogen to yield products of high economical and biological impact. Herein, we report a versatile and environmentally friendly protocol for the one‐pot synthesis of 2, 3‐dihydroquinazolin‐4(1 H )‐ones, a privileged scaffold in medicinal chemistry, based on the use of glucose as an eco‐friendly reductant in alkaline aqueous medium. This method can be viewed as a blueprint for the development of further one‐pot sequences involving glucose as a reductant. Abstract : The synthesis of 2, 3‐dihydroquinazolin‐4(1 H )‐ones in a one‐pot cascade manner (nitrile hydration, nitro‐reduction, imine formation, and cyclocondensation) is reported. Glucose, a renewable resource, can be easily obtained from abundant lignocellulosic biomass and was employed as a mild reductant in alkaline aqueous medium with 2‐nitrobenzonitrile.