53905-19-4Relevant academic research and scientific papers
Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions
Xie, Zongbo,Lan, Jin,Zhu, Haibo,Lei, Gaoyi,Jiang, Guofang,Le, Zhanggao
supporting information, p. 1427 - 1431 (2020/11/02)
A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.
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.
Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generatedin situ viaC=C bond cleavage
Xie, Zongbo,Lan, Jin,Yan, Liyuan,Chen, Xuehua,Li, Qian,Meng, Jia,Le, Zhanggao
, p. 2436 - 2441 (2021/04/02)
This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides andin situ-generated aldehydes. The latter was formedviaC=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with ano-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.
Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives
Yang, Jiangnan,Xie, Zongbo,Chen, Zhongsheng,Jin, Liang,Li, Qian,Le, Zhanggao
, p. 1496 - 1501 (2021/05/03)
A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.
Synthesis and in vitro Leishmania promastigote growth inhibition efficacy of novel 4(3H)-quinazolinone derivatives
Ralph, Greg L.,Zuma, Nonkululeko H.,Aucamp, Janine,N'Da, David D.
, p. 39 - 58 (2020/10/30)
Molecular hybridization is an increasingly important strategy in rational drug design and development. A series of novel quinazolinone-triazole hybrids have been synthesized and their antileishmanial activity investigated. Derivatives (E)-3-(prop-2-yn-1-yl)-2-styrylquinazolin-4(3H)-one, and (E)-3-{[1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-2-styrylquinazolin-4(3H)-one were observed to moderately inhibit the growth of promastigotes. An overall lack of significant antileishmanial activity may be attributable to the poor aqueous solubility of the derivatives. Future research endeavors will focus on potential remediation by investigating the anchoring of hydrophilic moieties to the quinazolinone scaffold.
C2-substituted quinazolinone derivatives exhibit A1 and/or A2A adenosine receptor affinities in the low micromolar range
Pieterse, Lianie,Terre'Blanche, Gisella,van der Walt, Mietha M.
supporting information, (2020/06/08)
Antagonists of the adenosine receptors (A1 and A2A subtypes) are widely researched as potential drug candidates for their role in Parkinson's disease-related cognitive deficits (A1 subtype), motor dysfunction (A2A subtype) and to exhibit neuroprotective properties (A2A subtype). Previously the benzo-α-pyrone based derivative, 3-phenyl-1H-2-benzopyran-1-one, was found to display both A1 and A2A adenosine receptor affinity in the low micromolar range. Prompted by this, the α-pyrone core was structurally modified to explore related benzoxazinone and quinazolinone homologues previously unknown as adenosine receptor antagonists. Overall, the C2-substituted quinazolinone analogues displayed superior A1 and A2A adenosine receptor affinity over their C2-substituted benzoxazinone homologues. The benzoxazinones were devoid of A2A adenosine receptor binding, with only two compounds displaying A1 adenosine receptor affinity. In turn, the quinazolinones displayed varying degrees of affinity (low micromolar range) towards the A1 and A2A adenosine receptor subtypes. The highest A1 adenosine receptor affinity and selectivity were favoured by methyl para-substitution of phenyl ring B (A1Ki = 2.50 μM). On the other hand, 3,4-dimethoxy substitution of phenyl ring B afforded the best A2A adenosine receptor binding (A2AKi = 2.81 μM) among the quinazolinones investigated. In conclusion, the quinazolinones are ideal lead compounds for further structural optimization to gain improved adenosine receptor affinity, which may find therapeutic relevance in Parkinson's disease-associated cognitive deficits and motor dysfunctions as well as exerting neuroprotective properties.
A Facile Microwave and SnCl2Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones
O'brien, Nicholas S.,McCluskey, Adam
, p. 1176 - 1186 (2020/10/06)
An elegantly simple, facile, and robust approach to a scaffold of biological importance, 2,3-dihydroquinazolin-4(1H)-ones, is reported. A catalytic 1 % SnCl2/microwave-mediated approach afforded access to pure material, collected by cooling and filtration after 20-min microwave irradiation at 120°C. A total of 41 analogues were prepared in isolated yields of 17-99 %. This process was highly tolerant of aliphatic, aromatic, heterocyclic, and acyclic aldehydes, but furan, pyrrole, and thiophene aldehyde reactivity correlated with propensity towards electrophilic addition and/or Diels-Alder addition. As a result, thiophene afforded high yields (80 %) whereas pyrrole carboxaldehyde failed to react. With simple cinnamaldehydes, and in the SbCl3-mediated reaction, and with α,β-unsaturated aldehydes the equivalent quinazolin-4(3H)-ones, and not the 2,3-dihydroquinazolin-4(1H)-ones, was favoured.
A quinazolinone of heterocyclic compound synthetic method
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Paragraph 0087-0090, (2019/07/01)
The invention discloses a quinazolinone of heterocyclic compound synthetic method. In under the action of the water-soluble alkali using air as the oxidizing agent, and ortho-amino alcohol oxidation fragrant nitrile compound - cyclized - oxidation of high efficiency series reaction one-step preparation quinazolinone of heterocyclic compound synthetic method. This method does not need the use of expensive transition metal catalyst and ligand, but the use of water-soluble alkali as promoter, the alkali can be removed by water washing mode is convenient, so product transition metal-free residue, is suitable as a pharmaceutical preparation of the precursor, the method condition is simple, easy to operate, low requirement for the device, and can utilizes air as economic security green oxidizing agent, water-soluble alkali as promoter, the only by-product is water, atom economical high, has a certain research and industrial application prospect.
Iridium(III)-Catalyzed Alkynylation of 2-(Hetero)arylquinazolin-4-one Scaffolds via C-H Bond Activation
Rohokale, Rajendra S.,Kalshetti, Rupali G.,Ramana, Chepuri V.
supporting information, p. 2951 - 2961 (2019/02/26)
The directed C-H alkynylation of 2-(hetero)arylquinazolin-4-ones has been explored with the ethynylbenziodoxolone reagent TIPS-EBX employing an Ir(III) catalyst. Complementary conditions for either monoalkynylation or dialkynylation have been developed. Also demonstrated is the broad scope of this reaction and the compatibility of various functional groups such as ?F, ?Cl, ?Br, ?CF3, ?OMe, ?NO2, and alkyl, etc.
One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies
Cao, Liu,Huo, Hengrui,Zeng, Haipeng,Yu, Yu,Lu, Dengfu,Gong, Yuefa
supporting information, p. 4764 - 4773 (2018/11/10)
A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).
