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3-methyl-2-phenylquinazolin-4(3H)-one is a heterocyclic organic compound characterized by a quinazolinone core structure, which features a fused benzene ring and a pyrimidine ring. 3-methyl-2-phenylquinazolin-4(3H)-one is specifically noted for its methyl group at the 3-position and a phenyl group at the 2-position, which contribute to its chemical properties and potential applications. It is often synthesized for use in medicinal chemistry, particularly in the development of anticancer and antiviral agents, due to its ability to interact with various biological targets. The compound's structure allows for further functionalization and modification, making it a versatile building block in the design of new pharmaceuticals.

22686-81-3

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22686-81-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 22686-81-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,6,8 and 6 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 22686-81:
(7*2)+(6*2)+(5*6)+(4*8)+(3*6)+(2*8)+(1*1)=123
123 % 10 = 3
So 22686-81-3 is a valid CAS Registry Number.

22686-81-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-methyl-2-phenylquinazolin-4-one

1.2 Other means of identification

Product number -
Other names 3-Methyl-2-phenyl-4-oxo-3,4-dihydro-chinazolin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22686-81-3 SDS

22686-81-3Relevant academic research and scientific papers

Access to 2-Arylquinazolin-4(3H)-ones through Intramolecular Oxidative C(sp3)?H/N?H Cross-Coupling Mediated by I2/DMSO

Wen, Simiaomiao,Du, Yifan,Liu, Yiwen,Cui, Xiaofeng,Liu, Qixing,Zhou, Haifeng

, (2021/12/01)

A novel approach for the synthesis of 2-arylquinazolin-4(3H)-ones was developed. A series of title compounds were obtained with good functional group tolerance and good yields by I2/DMSO-mediated intramolecular oxidative cross-coupling of 2-(benzylamino)benzamides to form C=N double bonds. This method was applicable for gram-scale synthesis. A proposed reaction pathway based on some control experiments was also provided.

Synthesis of quinazolin-4(3H)-ones via electrochemical decarboxylative cyclization of α?keto acids with 2-aminobenzamides

Tian, Qing,Wei, Yu,Xu, Liang,Zhang, Jinli

, (2021/01/05)

Herein, an environmentally benign electrochemical protocol has been disclosed for the synthesis of quinazolin-4(3H)-one derivatives from readily available α?keto acids and 2-aminobenzamides. This decarboxylative cyclization process proceeds conveniently in the absence of any homogeneous metal catalysts, bases, or external oxidants. This protocol also features CO2 by-products, mild reaction conditions (room temperature and air atmosphere), and a wide variety of substrate scope, including an array of 2,3-disubstituted quinazolinone products.

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan

, p. 14866 - 14882 (2021/10/25)

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2-Aryl Quinazolinones Utilizing the π-Benzylpalladium(II) System in Water

Hikawa, Hidemasa,Nakayama, Taku,Takahashi, Makiko,Kikkawa, Shoko,Azumaya, Isao

supporting information, p. 4075 - 4084 (2021/07/26)

We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides followed by an amide-directed benzylic C?H amination process utilizing the π-benzylPd(II) system. Comparison of independent rate measurements using benzyl alcohol and its deuterated form gave a kinetic isotope effect of 3.5. Therefore, the benzylic C?H bond is cleaved in the rate-determining step. We successfully carried out a gram-scale reaction in 85% yield with simplified product isolation. (Figure presented.).

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.

Direct synthesis of quinazolinones via the carbon-supported acid-catalyzed cascade reaction of isatoic anhydrides with amides and aldehydes

Zhang, Xiangyu,Luo, Chujun,Chen, Xiaoyong,Ma, Weilin,Li, Bin,Lin, Zirui,Chen, Xiuwen,Li, Yibiao,Xie, Feng

, (2021/02/20)

A novel catalytic system is reported for the construction of quinazolinones via the carbon-supported acid-catalyzed cascade coupling of isatoic anhydrides with amides and aldehydes. Subsequent selective hydrosilylation of the quinazolinones using a hydrogen-transfer strategy was also explored to provide dihydroquinazolines with structural diversity. The developed methodology proceeds with a broad substrate scope, excellent functional group tolerance, and utilizes a reusable catalyst and air as a green oxidant.

An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols

Dong, Yibo,Wu, Yangjie,Yan, Congcong,Yang, Jinchen,Zhang, Jinli

supporting information, p. 15344 - 15349 (2021/09/07)

An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes

Nomula, Vishnuvardhan,Rao, Sadu Nageswara

supporting information, p. 2602 - 2612 (2021/08/03)

KOtBu-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes have been developed. In this protocol, a variety of nitriles as well as aldehydes react with 2-substituted benzamides to corresponding quinazolin-4(3H)-ones products in good to moderate yields, via the cleavage of C-X and C-N bonds and the formation of double C-N bonds simultaneously, in presence of potassium tert-butoxide.

Method for preparing 2 -phenyl quinazolinone compound

-

Paragraph 0054-0056, (2021/10/30)

The invention relates to a preparation method of 2 -phenyl quinazolinone compounds, in particular to II. To the method, 2 - (benzylamino) benzamide compound (I) is used as a raw material for reaction of the experiment model, a simple substance iodine cata

Complementary Reactivity in Selective Radical Processes: Electrochemistry of Oxadiazolines to Quinazolinones

Hwang, Ho Seong,Cho, Eun Jin

supporting information, p. 5148 - 5152 (2021/07/19)

Electrochemistry has recently emerged as a sustainable approach for efficiently generating radical intermediates utilizing eco-friendly electric energy. An electrochemical process was developed to transform 1,2,4-oxadiazolines under mild conditions. The electrochemical N-O bond cleavage at a controlled oxidation potential led to the selective synthesis of quinazolinone derivatives that could not be obtained by photocatalytic radical processes, indicating complementary reactivities in radical processes. The electrochemical reaction pathways were fully revealed by density functional theory-based investigations.

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