36384-00-6

Upstream product

• 4424-17-3 2-aminobenzanilide 
• 62-53-3 aniline 
• 118-48-9 isatoic anhydride 
• 21258-59-3 2-(methylamino)-N-phenylbenzamide 
• 110-71-4 1,2-dimethoxyethane 
• 21097-36-9 N¹-methyl-N³-phenyl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one 

Relevant academic research and scientific papers

Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one

Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.

IBX-mediated synthesis of indazolone via oxidative N-N bond formation and unexpected formation of quinazolin-4-one: In situ generation of formaldehyde from dimethoxyethane

Synthesis of indazolone derivatives, which exhibit diverse biological and pharmaceutical activities, were achieved by hypervalent λ5 iodine reagents, such as iodoxybenzoic acid (IBX),-mediated oxidative N-N bond forming cyclization. In this study, the equivalence of IBX was optimized to promote the formation of N-N bond by oxidatively generated acylnitrenium ion. Dimethoxyethane and dichloroethane were discovered as alternative solvents and the reaction could be conducted in more concentrated condition. Some unprecedented substrates successfully afforded the corresponding indazolone in new condition discovered in this study. When the reactions were conducted in DME solvent, substrates with no electron-rich phenyl substituted amides afforded the unanticipated quinazolin-4-ones in moderate yields, which were not formed in DCE solvent. The formation of quinazolin-4-ones was attributed to the in situ generation of formaldehyde from DME. Therefore, the reaction might undergo different pathway in DME when the substrate aryl amides have phenyl rings without electron donating substituents.

Nickel boride mediated reductive desulfurization of 2-thioxo-4(3H)-quinazolinones: A new synthesis of quinazolin-4(3H)-ones and 2,3-dihydro-4(1H)-quinazolinones

A novel one-pot approach for the synthesis of aryl substituted quinazolin-4(3H)-ones and 2,3-dihydro-4(1H)-quinazolinones has been reported based on the reductive desulfurization of 3-aryl-2-thioxo-4(3H)-quinazolinones with nickel boride in dry methanol at ambient temperature.