76285-47-7

Usage

Class of organic compound

quinazolinone derivative

Contains

phenylmethyl group, methylene group, and hydrogen group attached to the quinazolinone ring

Used in

pharmaceutical industry for the synthesis of compounds with potential biological activities (e.g. antiviral, antitumor)

Also used as

building block in organic synthesis and chemical research

Upstream product

• 551-93-9 2-aminoacetophenone 
• 1198564-90-7 N'-benzyl-N-(2-ethynylphenyl)urea 
• 3173-56-6 benzyl isothiocyanate 
• 100-46-9 benzylamine 
• 1504-06-9 3-methylindolin-2-one 
• 143073-58-9 3-Benzyl-4-hydroxy-4-methyl-2-thioxo-1,2,3,4-tetrahydro-chinazolin 
• 134470-65-8 1-(2-isothiocyanatophenyl)ethan-1-one 
• 143073-59-0 3-Benzyl-4-methylen-2-thioxo-1,2,3,4-tetrahydrochinazolin 

Downstream Products

• 76285-48-8 3-benzyl-4-methyl-3,4-dihydro-2(1H)-quinazolinone 
• 1932-42-9 3-benzylquinazoline-2,4-dione 

Relevant academic research and scientific papers

Expeditious Approach to Indoloquinazolinones via Double Annulations of o-Aminoacetophenones and Isocyanates

A novel procedure for a one-pot cascade reaction of o-aminoacetophenones and aryl/aliphatic isocyanates catalyzed/oxidized by the [Pd]/[Ag] system was developed. The reaction involves two C-N bond and one C-C bond formations during the double annulation process and the desired indoloquinazolinones and derivatives were afforded up to 81% yields from readily available substrates with a tolerance of a broad variety.

Sequential Oxidative Fragmentation and Skeletal Rearrangement of Peroxides for the Synthesis of Quinazolinone Derivatives

For the first time, the sequential reaction of peroxyoxindole that involves base-promoted oxidative fragmentation to isocyanate formation and primary amine or amino alcohol accelerated skeletal rearrangement to synthesize exo-olefinic-substituted quinazolinone or oxazoloquinazolinone is reported. The advantages of this new reaction include a broad substrate scope and transition-metal-free and room-temperature conditions. The formation of the isocyanate as a key intermediate that accelerates oxidative skeletal rearrangement has been confirmed by trapping experiments and spectroscopic evidence.

Preparation method of 4-methylene quinazolinone (thione) derivatives

The invention discloses a preparation method of 4-methylene quinazolinone (thione) derivatives. The preparation method comprises the following steps: dissolving 2-aminoacetophenone derivatives with different substituents and phenyl iso (thio) cyanate deri

Facile preparation of 3-substituted 2-quinazolinones via electrogenerated base

A new series of 3,4-disubstituted quinazolin-2-ones, with potential T-type calcium channel antagonist activity, and new 4-methylene-quinazolin-2-ones, promising catalysts as N-heterocyclic olefins, have been prepared in good yield by a simple reaction between 2-aminobenzophenone, or 2-aminoacetophenone, and cyanomethyl anion electrogenerated by acetonitrile reduction at a graphite electrode, followed by the addition of different organic isocyanates and subsequent heterocyclization.

NHC-stabilized gold(I) complexes: Suitable catalysts for 6-exo-dig heterocyclization of 1-(o-Ethynylaryl)ureas

Figure presented 3-substituted 1-(o-ethynylaryl)ureas 1 selectively undergo either 6-exo-dig or 5-endo-dig cyclization (to give 4-methylene-3,4-quinazolin- 2-ones 2 or indoles 3, respectively) depending on the choice of the metal, ligand, and reaction conditions. The best results (up to 96% yield) in the preparation of the hydroamination products 2 are achieved with the highly bulky NHC-stabilized cationic gold(I) complex [Au(IPr)]+. Conversely, ureas bearing an internal alkyne lead to the 5-endo-dig cyclization mode regardless of the gold(I) complex employed. Whereas the nature of the substituent at N-3 does not have any influence on the regiochemistry observed, it does, in some cases, affect the efficiency of these transformations.