62820-49-9Relevant academic research and scientific papers
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.).
Development of a New Synthetic Method for Quinazolinones via Aerobic Oxidation in dimethylsulfoxide
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Paragraph 0171-0174; 0199-0202, (2021/03/30)
The present invention relates to a method for preparing quinazoline derivatives by aerobic oxidation using oxygen as an oxidizing agent in dimethylsulfoxide (DMSO) solvent wherein metal and base are excluded. The method for preparing quinazoline derivatives according to the present invention does not require any metal catalyst such as palladium or iridium, and thus does not cause toxicity problem of residual metal; and does not require demanding processes such as strong acid, or base conditions, low temperature reactions, or reactions of anhydrous conditions and thus, it is possible to simply and economically prepare quinazoline derivatives by reacting anthranilamide derivatives and an aldehyde source.
Synthesis of quinazolinones from anthranilamides and aldehydes via metal-free aerobic oxidation in DMSO
Kim, Na Yeun,Cheon, Cheol-Hong
supporting information, p. 2340 - 2344 (2014/05/06)
A highly environmentally benign protocol for the synthesis of quinazolinones from anthranilamides and aldehydes via aerobic oxidation was developed in wet DMSO. This protocol is operationally simple, exhibits broad substrate scope, and does not need toxic metal catalysts and bases. In addition, the utility of this transformation was further demonstrated by converting the resulting quinazolinones into other useful products in the same-pot without their isolation.
A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones
Dabiri, Minoo,Salehi, Peyman,Bahramnejad, Mahboobeh,Alizadeh, Mohsen
experimental part, p. 877 - 881 (2011/06/26)
An effective one-pot three-component route to 4(3H)-quinazolinones from commercially available starting materials is reported. Thus, isatoic anhydride reacted with ammonium acetate or primary amines and aldehydes in the presence of iodine to produce the corresponding quinazolinone derivatives in moderate to good yields. Springer-Verlag 2010.
Palladium-catalyzed cyclocarbonylation of o-lodoanilines with Imidoyl Chlorides to produce quinazolin-4(3H)-ones
Zheng, Zhaoyan,Alper, Howard
supporting information; experimental part, p. 829 - 832 (2009/04/07)
A wide variety of substituted quinazolin-4(3H)-ones were prepared in 63-91% yields by the palladium-catalyzed cyclocarbonylation of o-iodoanilines with imidoyl chlorides and carbon monoxide. The reaction is believed to proceed via in situ formation of an amidine, followed by oxidative addition, CO insertion, and intramolecular cyclization to give the substituted quinazolin-4(3H)-ones.
