491-36-1Relevant articles and documents
Application of organolithium in organic synthesis: A simple and convenient procedure for the synthesis of more complex 6-substituted 3H-quinazolin-4-ones
El-Hiti, Gamal A.
, p. 323 - 331 (2004)
6-Methyl-3H-quinazolin-4-one reacted with alkyllithium reagents at -78°C in THF to give 2-alkyl-1,2-dihydro-6-methyl-3H-quinazolin-4-ones in high yields. However, no reaction took place when LDA was used as the lithium reagent. 6-Bromo-3H-quinazolin-4-one reacted with excessive butyllithium to give 2-butyl-1,2-dihydro-3H-quinazolin-4-ones in very good yields. However, the lithiation of 6-bromo-3H-quinazolin-4-one was achieved by the use of a combination of methyllithium (1.1 equivalents) and tert-butyllithium (2.2 equivalents) at -78°C in THF. The dilithio reagent thus obtained reacted with a variety of electrophiles (H2O, iodoethane, benzaldehyde, anisaldehyde, cyclohexanone, 2-hexanone, benzophenone, phenyl isothiocyanate, TITD) to give the corresponding 6-substituted 3H-quinazolin-4-ones in excellent yields. Reaction of the dilithio reagent with 1,3-dibromopropane gave 6,6′-(propanediyl)bis(3H-quinazolin-4-one). Springer-Verlag 2003.
Synthesis and antifungal activities of N3-substituted quinazolin-4-one catalyzed by 3-Methylimidazole ionic liquids
Liu,Liu,Ji,Sun,Liu,Wen,Xu
, p. 9853 - 9856 (2013)
N3-Substituted quinazolin-4-one was synthesized by alkyl bromide and quinazolin-4-one was synthesized by anthranilic acid and formamide, catalyzing in various 3-methylimidazole ionic liquids and TBAB. The results showed that the yield of N3-substituted quinazolin-4-one increased appreciably and the reaction time shorted under ionic liquids and TBAB. Using 1-methyl-3-(2-hydroxyl-3- acetoxylpropyl)imidazolium fluoroborate or 1-propyl-3-methylimidazole fluoroborate as catalyst, the yield of N3-benzylquinazolin-4-one reached 85.1 and 82.0 %, increased 27 % more than the yield of traditional conditions. The compounds were evaluated for their in vitro antifungal activity against Fusarium graminearum, Fusarium oxysporum and Cytospora mandshurica. Compound 3f inhibited Fusarium graminearum with EC 50 28.85 μg/mL, Fusarium oxysporum with EC50 24.68 μg/mL and Cytospora mandshurica with EC50 37.67 μg/mL.
2-(3-ethyl-2,2-dimethylcyclobutyl-methyl)-4(3H)-quinazolinones
Avotin'sh,Petrova,Pastors,Strakov
, p. 722 - 728 (1999)
Anthranilic acid and its 5-bromo and 4-chloro derivatives react with pinanoic and pinonoic acid chlorides to give the corresponding N-acyl derivatives. The pinanoyl derivatives give the corresponding 2-(3-ethyl-2,2-dimethyl-cyclobutylmethyl)-4-(3H)-quinazolinones when refluxed in formamide. Pinanoylanthranilic acid reacts with dicyclohexylcarbodiimide to give 2-(3-ethyl-2,2-dimethyl-cydobutylmethyl)benz-3,1-oxazin-4(H)-one and subsequently with hydrazine hydrate to give 3-amino-2-(3-ethyl-2,2-dimethylcyclobutylmethyl)-4(3H)-quinazolinone. Refluxing of the pinanoyl- and pinonoylanthranilic acids with acetic anhydride gives acetylanthranilic acid, and pinonoylanthranilic acid gives 4(3H)-quinazolinone with formamide. 1999 KluwerAcademic/Plenum Publishers.
A new approach to the facile synthesis of 2-substituted-quinazolin-4(3H)- ones
Wang, Bin,Li, Zeng,Wang, Xiao Ning,Tan, Jia Heng,Gu, Lian Quan,Huang, Zhi Shu
, p. 951 - 953 (2011)
A new approach to the facile synthesis of 2-substituted-quinazolin-4(3H)- ones and its derivatives using the condensation reaction of substituted 2-aminobenzamide and orthoesters is reported.
Discovery of quinazolinyl-containing benzamides derivatives as novel HDAC1 inhibitors with in vitro and in vivo antitumor activities
Zhang, Zixue,Zhang, Qingwei,Zhang, Hao,Jiao, Minru,Guo, Zheng,Peng, Xinyan,Fu, Lei,Li, Jianqi
, (2021/10/16)
A series of quinazolinyl-containing benzamide derivatives were designed, synthesized and evaluated for their in vitro histone deacetylase 1 (HDAC1) inhibitory activities. Compounds 11a surpassed the known class I selective HDAC inhibitor MS-275 in both HDAC1 enzymatic inhibitory activity and cellular anti-proliferative activity against a selected set of cancer cell types (Hut78, K562, Hep3B and HCT116 cells) with no observed effects on human normal cells. In particular, compound 11a inhibited HDAC1 over the other tested HDACs isoforms (HDAC2, HDAC6 and HDAC8) with acceptable safety profiles. Moreover, compound 11a displayed favorable oral pharmacokinetic properties and showed significant antitumor activity in the A549 tumor xenograft model in vivo.
Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
Pal, Shantanu,Sahoo, Subrata
, p. 18067 - 18080 (2021/12/06)
A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.
