1806-68-4Relevant academic research and scientific papers
Vinylene carbonate: Beyond the ethyne surrogate in rhodium-catalyzed annulation with amidines toward 4-methylquinazolines
Wang, Chang,Fan, Xiaodong,Chen, Fan,Qian, Peng-Cheng,Cheng, Jiang
supporting information, p. 3929 - 3932 (2021/04/26)
In this paper, we developed a rhodium-catalyzed annulation of vinylene carbonate with amidines, leading to 4-methylquinazolines with moderate to excellent yields. This procedure proceeded by sequentialortho-acylation and annulation, where vinylene carbonate served as the acetylation reagent rather than the ethyne surrogate.
Potassium iodide-catalyzed three-component synthesis of 2-arylquinazolines via amination of benzylic C-H bonds of methylarenes
Zhao, Dan,Shen, Qi,Li, Jian-Xin
supporting information, p. 339 - 344 (2015/03/04)
A novel potassium iodide-catalyzed three-component synthesis of quinazolines via benzylic C-H bonds amination was developed. Commonly used ammonia salt and the sp3 carbon in commercially available methylarenes were used as nitrogen and C1 sources, respectively. Mechanistic studies indicated that an aryl aldehyde is involved as a key intermediate in the reaction.
Microwave-promoted syntheses of quinazolines and dihydroquinazolines from 2-aminoarylalkanone O-phenyl oximes
Portela-Cubillo, Fernando,Scott, Jackie S.,Walton, John C.
supporting information; experimental part, p. 4934 - 4942 (2009/12/01)
(Chemical Equation Presented) A wide range of biologically active compounds contain the quinazoline ring system. A new free-radical-based method of making functionalized quinazolines is described, which relies on microwave-promoted reactions of O-phenyl oximes with aldehydes. A small set of 2-aminoaryl alkanone O-phenyl oximes was prepared and shown to produce dihydroquinazolines when mixed with an aldehyde in toluene and subjected to microwave heating. When ZnCl2 was included in the reaction mixture, fully aromatic quinazolines were produced in high yields by a rapid and convenient process. The method worked well with alkyl, aryl, and heterocyclic aldehydes and for a variety of substituents in the benzenic part of the molecule. Similar reactions employing ketones instead of aldehydes were less efficient. Although some dihydroquinazolines did form, they were accompanied by several byproducts. Surprisingly, in each case, one of the byproducts was a quinoline derivative, and a plausible mechanism to account for this rearrangement is proposed.
2-(Aminoaryl)alkanone O-phenyl oximes: Versatile reagents for syntheses of quinazolines
Portela-Cubillo, Fernando,Scott, Jackie S.,Walton, John C.
body text, p. 2935 - 2937 (2009/02/03)
Microwave irradiations of 2-(aminoaryl)alkanone O-phenyl oximes and carbonyl compounds generate iminyl radicals in company with imines; iminyl on imine ring closure yields dihydroquinazolines or quinazolines when ZnCl 2 is included in the mixtu
