30838-16-5Relevant academic research and scientific papers
Unexpected Insertion of Nitrogen into a C-C Bond: Access to 2,3-Disubstituted Quinazolinone Scaffolds
Liu, Hui-Li,Li, Xiao-Tong,Tian, Heng-Zhi,Sun, Xing-Wen
supporting information, p. 4579 - 4583 (2021/06/28)
A novel, practical, highly efficient, and transition metal free nitrogen insertion reaction for the synthesis of 2,3-disubstituted quinazolinone derivatives was developed. Diverse functionalized 3-indolinone-2-carboxylates and nitrosoarenes with a wide range of substituted nitrosobenzenes, nitrosopyridines, dibenzofuranyl, or dibenzothienyl nitroso compounds worked smoothly to give 2,3-disubstituted quinazolinone derivatives in good to excellent yields (69-98%). A gram-scale reaction was achieved, and an afloqualone analogue was synthesized under the mild reaction conditions.
One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies
Cao, Liu,Huo, Hengrui,Zeng, Haipeng,Yu, Yu,Lu, Dengfu,Gong, Yuefa
supporting information, p. 4764 - 4773 (2018/11/10)
A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).
Synthesis of 3-aryl-2-[hydroxy(diaryl)methyl]-4-oxo-3,4-dihydroquinazolines
Shemchuk,Chernykh,Levashov,Sytnik,Shemchuk
scheme or table, p. 1687 - 1690 (2011/03/19)
By heating arylamides of N-ethoxalylanthranilic acid in the acetic acid mediun in the presence of triethylamine the corresponding ethyl 3-aryl-4-oxo-3,4-dihydroquinazoline-2-carboxylates were obtained. The latter in the conditions of the Grignard reaction formed 3-aryl-2-[hydroxy-(diaryl)methyl] -4-oxo-3,4-dihydroquinazolines. Pleiades Publishing, Ltd., 2010.
Synthetic studies on 3-arylquinazolin-4-ones: Intramolecular nucleophilic aromatic substitution reaction of 2-carboxamido-3-arylquinazolin-4-ones and its application to the synthesis of secondary aryl amines
Fuwa, Haruhiko,Kobayashi, Toshitake,Tokitoh, Takashi,Torii, Yukiko,Natsugari, Hideaki
, p. 4297 - 4312 (2007/10/03)
The general synthesis and a novel intramolecular nucleophilic aromatic substitution (SNAr) reaction of 2-carboxamido-3-arylquinazolin-4- ones, a potentially useful scaffold in the field of medicinal chemistry, are described. The synthetic utili
