76315-66-7

Upstream product

• 1022-45-3 2-phenyl-4(3H)-quinazolinone 
• 107-04-0 1-Bromo-2-chloroethane 
• 503856-76-6 4-(2-chloroethoxy)-2-phenylquinazoline 
• 67-66-3 chloroform 
• 67090-21-5 3-(2-hydroxyethyl)-2-phenyl-quinazoline-(3H)-4-one 
• 93-97-0 benzoic acid anhydride 
• 1570134-48-3 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)benzamide 
• 1885-29-6 anthranilic acid nitrile 
• 65-85-0 benzoic acid 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 28144-70-9 anthranilic acid amide 

Relevant academic research and scientific papers

Lewis-acid-promoted cyclization reaction: Synthesis of N3-chloroethyl and N3-thiocyanatoethyl quinazolinones

A Lewis-acid-promoted cyclization reaction of benzoyl chlorides with 2-(4,5-dihydrooxazol-2-yl)anilines, which can offer a series of N3-chloroethyl quinazolinones, is disclosed. The reaction is compatible with the functional groups of the substrates; environment-friendly AlCl3 is probably the chloride source. Moreover, the addition of NH4SCN can also produce a range of N3-thiocyanatoethyl quinazolinones in moderate-to-good yields.

Base-promoted Lewis acid catalyzed synthesis of quinazoline derivatives

A one-pot protocol has been developed for the synthesis of quinazolinones from amide-oxazolines with TsCl via a cyclic 1,3-azaoxonium intermediate and 6π electron cyclization in the presence of a Lewis acid and base. The process is operationally simple and has a broad substrate scope. This method provides a unique strategy for the construction of quinazolinones.

Studies on quinazolines. 11. Intramolecular imidate-amide rearrangement of 2-substituted 4-(ω-chloroalkoxy)quinazoline derivatives. 1,3 -O → N shift of chloroalkyl groups via cyclic 1,3-azaoxonium intermediates

The ω-chloroalkylation of 2-substituted quinazo lin-4(3H)-one derivatives 1 and 2 with Br-(CH2)n-Cl (n = 2-4) and the intramolecular imidate-amide rearrangement of the alkylated products are described. At room temperature, the 2-phenyl substituent promoted O-alkylation, whereas the less steric 2-benzyl group led to a higher ratio of N-alkylation. The investigation of the O-alkylated products, 4-ω-chloroalkoxyquinazolines, revealed that the migration of ω-chloroethyl and ω-chloropropyl groups from oxygen to nitrogen should be intramolecular via five- and six-membered cyclic 1,3-azaoxonium intermediates, respectively. Competition between rearrangement and nucleophilic substitution results in the formation of 7a,b and 8a,b from the nucleophilic substitution of 4a,b and 6a,b, respectively.

Piperidinylalkyl quinazoline compounds, composition and method of use

Novel quinazoline derivatives, comprising in the heterocyclic part of their quinazoline nucleus at least one carbonyl or thiocarbonyl group and a particularly substituted piperidinyl-alkyl side chain, said compounds being potent serotonin-antagonists.