1769-24-0Relevant articles and documents
Aluminium-containing ring systems and N-heterocycle formation via nitrile insertions into Al-N bonds
Gibson,Redshaw,White,Williams
, p. 79 - 80 (2001)
Reactions of Me3Al with 1,2-diaminobenzene [1,2-(H2N)2C6H4] or anthranilic acid, [1,2-(H2N)(HO2-C)C6H4], followed by treatment with acetonitrile, afford tetranuclear and hexanuclear aluminium-containing ring systems; a single crystal X-ray structure on the hexametallic product reveals the construction of quinazoline ligands arising via insertion of acetonitrile into Al-N bonds.
Infrared spectra, thermogravimetric analysis and antifungal studies of noval cr(iii), fe(iii) and cu(ii) 2-methyl-quinazolinone complexes
Sadeek,El-Attar,El-Lattif, N.S. Abd
, p. 53 - 66 (2014)
Some new solid complexes [CrCl3(L)3]×6H 23O, [FeCl3(L)3]×6H2O and [Cu(CH 3COO)2(L)3]×2H2O have been synthesized quantitatively by the interactions of 2-methyl-quinazolinone (L) with CrCl3.6H23O, FeCl3.6H2O and Cu(CH3COO)2. 2H2O in a mixture of an ethanol-bidistilled water (1:1), at 60 °C. They were characterized by melting point, molar conductivity, magnetic moment, elemental analysis, infrared spectra and thermal analyses. The results supported the formation of the complexes and indicated that the ligand reacted as a monodentate ligand bound to the metal ion through the oxygen atom. The antifungal activity of the free ligand and their metal complexes were evaluated against several species, such as Fusarium solani, Rizoctonia solani, Sclortium rolfsii and Botryodiplodia and they showed a good antifungal activity to some selected fungal strain as compared with free ligand.
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Siegle,Christensen
, p. 5777 (1951)
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Acylanthranils. 9. Influence of Hydrogen Bonding on the Reaction of Acetylanthranil with Ammonia
Errede, L. A.,Martinucci, P. D.,McBrady, J. J.
, p. 3009 - 3017 (1980)
It was shown that hydrogen bonding has a marked influence on the reaction of acetylanthranil (1) with ammonia.The product of the reaction in anhydrous benzene is 2-methylquinazolin-4-one (5, R = H) which is formed via pathway A as shown in Scheme I, but the rate of formation is unusually slow.The rate of this conversion is about 6 times faster in pyridine than in benzene.If water is added to the benzene system, the rate of reaction is increased by orders of magnitude, but the product is o-acetamidobenzamide (4, R = H) and not 5.In contrast to this result, the addition of water to the pyridine system causes a small decrease in rate and only a slight change in selectivity.These results are consistent with postulated mechanisms whereby 1 reacts with molecular clusters of ammonia, i.e. with (NH3)n in benzene, with N(H*S)3 in strong proton acceptor solvents S, and with (NH3)n*H2O in benzene plus added water.It was verified that cyclodehydration of 4 to give 5 occurs at an appreciable rate in aqueous solution at elevated temperatures and that this rate is accelerated considerably by the presence of strong base even at room temperature.It was also observed that o-acetamidobenzamide exists in at least two crystalline forms, α and β, which have different physical properties.
Unexpected Products from Carbonylation of Lithiated Quinazolin-4(3H)-one Derivatives
Smith,El-Hiti,Abdel-Megeed
, p. 430 - 435 (2003)
Doubly lithiated 3-pivaloylaminoquinazolin-4(3H)-one reacts with carbon(II) oxide at 0°C to give 77% of a mixture of azetidinone and indole derivatives, each incorporating a diisopropylamide unit from lithium diisopropylamide used for lithiation. No analogous reaction occurs with doubly lithiated 3-acetyl-aminoquinazolin-4(3H)-one and 3-acyl-2-alkylquinazolin-4(3H)- one. Carbonylation of doubly lithiated 2-alkyl-3-aminoquinazolin-4(3H)-ones at 0°C results in deamination to give 2-alkylquinazolin-4(3H)-ones in good yields.
Heterocyclic compounds; IX. A facile synthesis of methaqualone and analogs
Manhas,Amin,Rao
, p. 309 - 310 (1977)
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Design, Synthesis, and Structure-Activity Relationship of Quinazolinone Derivatives as Potential Fungicides
Peng, Jing-Wen,Yin, Xiao-Dan,Li, Hu,Ma, Kun-Yuan,Zhang, Zhi-Jun,Zhou, Rui,Wang, Yu-Ling,Hu, Guan-Fang,Liu, Ying-Qian
, p. 4604 - 4614 (2021/05/06)
Plant diseases caused by phytopathogenic fungi reduce the yield and quality of crops. To develop novel antifungal agents, we designed and synthesized eight series of quinazolinone derivatives and evaluated their anti-phytopathogenic fungal activity. The bioassay results revealed that compounds KZL-15, KZL-22, 5b, 6b, 6c, 8e, and 8f exhibited remarkable antifungal activity in vitro. Especially, compound 6c displayed the highest bioactivity against Sclerotinia sclerotiorum, Pellicularia sasakii, Fusarium graminearum, and Fusarium oxysporum, displaying appreciable IC50 values (50% inhibitory concentration) of 2.46, 2.94, 6.03, and 11.9 μg/mL, respectively. A further mechanism interrogation revealed abnormal mycelia, damaged organelles, and changed permeability of cell membranes in S. sclerotiorum treated with compound 6c. In addition, the in vivo bioassay indicated that compound 6c possessed comparable curative and protective effects (87.3 and 90.7%, respectively) to the positive control azoxystrobin (89.5 and 91.2%, respectively) at 100 μg/mL concentration against S. sclerotiorum. This work validated the potential of compound 6c as a new and promising fungicide candidate, contributing to the exploration of potent antifungal agents.
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.
