67796-16-1Relevant articles and documents
Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2-Aryl Quinazolinones Utilizing the π-Benzylpalladium(II) System in Water
Hikawa, Hidemasa,Nakayama, Taku,Takahashi, Makiko,Kikkawa, Shoko,Azumaya, Isao
supporting information, p. 4075 - 4084 (2021/07/26)
We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides followed by an amide-directed benzylic C?H amination process utilizing the π-benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C?H bond is cleaved in the rate-determining step. We successfully carried out a gram-scale reaction in 85% yield with simplified product isolation. (Figure presented.).
Method for synthesizing quinazolinone compound under photocatalysis condition
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Paragraph 0024-0027, (2020/08/12)
The invention belongs to the technical field of compound preparation. The invention discloses a method for synthesizing a quinazolinone compound under a photocatalysis condition. The method comprisesthe following step: by taking a compound shown as a formula I and a compound shown as a formula II as raw materials and copper salt or nickel salt or iron salt as a catalyst, performing a cyclizationreaction in a nitrogen atmosphere, an illumination condition, an oxygen atmosphere and an illumination condition in sequence under the action of an alkali and a solvent to synthesize the quinazolinonecompound shown as a formula III. According to the method, under the illumination condition, o-halogen benzamide can not only react with fatty amine, but also react with benzylamine to obtain the quinazolinone compound.
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.).