4260-34-8Relevant academic research and scientific papers
Chemoselective Reactions of Isocyanates with Secondary Amides: One-Pot Construction of 2,3-Dialkyl-Substituted Quinazolinones
Lin, Yi,He, Shu-Fan,Geng, Hui,Xiao, Yu-Chen,Ji, Kan-Lei,Zheng, Jian-Feng,Huang, Pei-Qiang
, p. 5345 - 5353 (2021)
A facile method for the preparation of 2,3-dialkyl-substituted quinazolinones from readily available N-arylamides and commercial isocyanates was developed. This one-pot procedure involves the chemoselective activation of the secondary amide with Tf2O/2-Br-Pyr, the sequential addition of isocyanate, and cyclization. The mild reaction is general for a wide range of substrates and can be run on a gram scale.
A novel superparamagnetic powerful guanidine-functionalized γ-Fe2O3based sulfonic acid recyclable and efficient heterogeneous catalyst for microwave-assisted rapid synthesis of quinazolin-4(3H)-one derivatives in Green media
Foroughifar, Naser,Khajeh-Amiri, Alireza,Norouzi, Fateme Haji,Pasdar, Hoda
, p. 29948 - 29959 (2021/10/20)
The novel organic-inorganic nanohybrid superparamagnetic (γ-Fe2O3@CPTMS-guanidine@SO3H) nanocatalyst modified with sulfonic acid represents an efficient and green catalyst for the one-pot synthesis of quinazolin-4(3H)-one derivativesviathree-component condensation reaction between anthranilic acid, acetic anhydride and different amines under microwave irradiation and solvent-free conditions (4a-q). XRD, FT-IR, FE-SEM, TGA, VSM and EDX were used to characterize this new magnetic organocatalyst. Outstanding performance, short response time (15-30 min), simple operation, easy work-up procedure, and avoidance of toxic catalysts can be regarded as its significant advantages. Moreover, it can be easily separated from the reaction solution through magnetic decantation using an external magnet, and recycled at least six times without notable reduction in its activity.
α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocyclesviadecarboxylative oxidative annulation reaction
Jung, Chanhyun,Jung, Jae-Kyung,Lee, Heesoon,Lee, Kiho,Lee, Seohu,Park, Yunjeong,Sim, Jaeuk,Viji, Mayavan,Vishwanath, Manjunatha
, p. 37202 - 37208 (2020/10/28)
A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and indolo[1,2-a]quinoxaline has been developed. The key features of our method include thein situgeneration of aldehyde from α-hydroxy acid in the presence of TBHP (tert-butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields.
Approach to the Synthesis of 2,3-Disubstituted-3H-quinazolin-4-ones Mediated by Ph3P-I2
Phakhodee, Wong,Wangngae, Sirilak,Pattarawarapan, Mookda
, p. 8058 - 8066 (2017/08/14)
Readily available N-substituted amides or their requisite carboxylic acids or acid chlorides have been used to construct 2,3-disubstituted-3H-quinazolin-4-ones in a one-pot procedure. Key transformation in this convergent approach involves Ph3P-I2-mediated formation of amidine upon condensation of an amide or the intermediate amide with methyl anthranilate. Cyclization of the amidine-tethered anthranilate then affords 2,3-disubstituted-3H-quinazolin-4-ones in good to excellent yields under mild conditions.
A quinazoline compound and its synthesis method
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Paragraph 0108-0111, (2017/11/16)
The invention discloses a synthetic method of a quinazolinone compound. The method can be used for preparing the quinazolinone compound by carrying out reaction at a proper temperature and time by taking a 2-aminobenzamide derivative and a 1, 3-diketone compound as raw materials, taking chiral Bronsted acid or Lewis acid as a catalyst and water and biodegradable ethyl lactate and polyethylene glycol as a mixed solvent. The synthetic method of the quinazolinone compound provided by the invention is mild in reaction condition, low in cost, environment-friendly, high in yield and suitable for industrial production.
Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives
Xu, Wei,Zhu, Xiao-Rui,Qian, Peng-Cheng,Zhang, Xing-Guo,Deng, Chen-Liang
supporting information, p. 2851 - 2857 (2016/12/16)
We developed a copper-catalyzed tandem reaction of 2-aminobenzamides with tertiary amines for the formation of quinazolinone derivatives. The strategy includes two steps (cyclization and coupling) performed in one pot. A number of substrates reacted well under standard conditions to give the corresponding quinazolinone derivatives in moderate to good yields.
FeCl3-catalyzed tandem condensation/intramolecular nucleophilic addition/C-C bond cleavage: A concise synthesis of 2-substitued quinazolinones from 2-aminobenzamides and 1,3-diketones in aqueous media
Shen, Guanshuo,Zhou, Haifeng,Sui, Yuebo,Liu, Qixing,Zou, Kun
supporting information, p. 587 - 590 (2016/01/20)
A concise approach for the synthesis of 2-substituted quinazolinones using an iron-catalyzed tandem reaction of 2-aminobenzamides with acyclic or cyclic 1,3-diketones via condensation, intramolecular nucleophilic addition, C-C bond cleavage in an aqueous solution of poly(ethylene glycol) under oxidant-free conditions has been developed.
Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: Applications towards the synthesis of drugs
Kumar, Dinesh,Jadhavar, Pradeep S.,Nautiyal, Manesh,Sharma, Himanshu,Meena, Prahlad K.,Adane, Legesse,Pancholia, Sahaj,Chakraborti, Asit K.
, p. 30819 - 30825 (2015/04/22)
Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions. The multicomponent reaction (3-MCR) involving isatoic anhydride, an amine, and orthoester afforded the 2,3-disubstituted quinazolin-4(3H)-ones in excellent yields under classical heating at 120 °C for 5 h or under microwave irradiation at 140°C for 20-30 min. The use of ammonium acetate instead of the amine provides the 2-substituted quinazolin-4(3H)-ones. The reactions are compatible with various substituted isatoic anhydrides, aryl/heteroaryl/alkyl/cycloalkyl amines, and orthoesters. The strategies are extended to the one pot tandem condensation involving isatoic anhydride, an amine, orthoester, and aldehyde to afford highly functionalized (E)-3-aryl/heteroaryl-2-styrylquinazolin/(2-(heteroaryl)vinyl)quinazolin-4(3H)-ones. The applications of the methodologies are demonstrated through the synthesis of various drugs which act on the central nervous system such as methaqualone, mebroqualone, mecloqualone, piriquialone, and diproqualone.
Br?nsted acid-catalyzed selective C-C bond cleavage of 1,3-diketones: A facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate
Shen, Guanshuo,Zhou, Haifeng,Du, Peng,Liu, Sensheng,Zou, Kun,Uozumi, Yasuhiro
, p. 85646 - 85651 (2015/11/03)
A facile and green approach was developed for the synthesis of 4(3H)-quinazolinones by using camphorsulfonic acid as a catalyst in an aqueous solution of biodegradable ethyl lactate. Various 2-aryl-, 2-alkyl-, and 2-(4-oxoalkyl)quinazolinones were obtained by cyclization of 2-aminobenzamides with a wide range of acyclic or cyclic 1,3-diketones via C-C bond cleavage in satisfactory to excellent yields.
Syntheses of quinazolinones from 2-iodobenzamides and enaminones via copper-catalyzed domino reactions
Songsichan, Teerawat,Promsuk, Jaturong,Rukachaisirikul, Vatcharin,Kaeobamrung, Juthanat
supporting information, p. 4571 - 4575 (2014/06/24)
N-Substituted 2-iodobenzamides and enaminones undergo cascade transformations to achieve quinazolinones via a copper-catalyzed Ullmann-type coupling, a Michael addition and a retro-Mannich reaction. A unique stereochemical feature of this domino process was that Z-enaminones reacted without external ligands, whereas E-enaminones required the assistance of ligands. This journal is
