60444-92-0Relevant academic research and scientific papers
Copper-Catalyzed Self-Condensation of Benzamide: Domino Reactions towards Quinazolinones
Sayyad, Nisar,Cele, Zamani,Aleti, Rajeshwar Reddy,Bera, Milan,Cherukupalli, Srinivasulu,Chandrasekaran, Balakumar,Kushwaha, Narva Deshwar,Karpoormath, Rajshekhar
supporting information, p. 5382 - 5388 (2018/10/20)
We herein report a simple and highly efficient microwave-assisted, copper-catalyzed and ligand-free synthetic method for 2-substituted 4(3H)-quinazolinones as domino reaction. This reaction proceeds via self-condensation of substrate (2-bromo/iodo benzamide) in the presence of a strong base and copper catalyst. The substituted quinazolinones were obtained in one-pot reaction by intramolecular cyclization (condensation) via Ullmann–type intermediate. Both the intermediates and quinazolinones were obtained in good yield and can be further used as building blocks for developing the potential novel drug-like compounds.
Pd-catalysed ortho-alkoxylation of benzamides N-protected with an iminophosphorane functionality
Villuendas, Pedro,Serrano, Elena,Urriolabeitia, Esteban P.
, p. 3077 - 3083 (2015/04/22)
The oxidative coupling of keto-stabilised iminophosphoranes (IPs) Ph3P=NC(O)C6HxRy with alcohols R′OH affords the alkoxylated species Ph3P=NC(O)C6Hx-1Ry-2-OR′. The process is catalysed by 10% PdCl2(NCMe)2, uses oxone as an oxidant and alcohol R′OH as a source of OR′ groups and reaction solvent. The reaction takes place at room temperature regioselectively at the ortho-position of the benzamide ring, gives only the mono-alkoxylated derivatives, and shows tolerance to a variety of functional groups and different primary and secondary alcohols. Better yields were obtained when the aryl ring contains electron-releasing substituents (OMe, Me). The iminophosphorane moiety plays a dual role as the protecting/directing group, and can be hydrolysed to give the corresponding free benzamide.
