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72-44-6Relevant articles and documents
Synthesis of methaqualone and its diphasic titration in pure and tablet forms
Soliman,Shafik,Elnenaey
, p. 411 - 413 (1978)
A one-step synthesis of methaqualone from N-acetylanthranilic acid and O-toluidine in the absence of a catalyst is described. A rapid diphasic titration procedure for its microestimation in pure and tablet forms, using dioctyl sulfosuccinate and dimethyl yellow screened with oracet blue B, is proposed. The data were compared with those obtained from nonaqueous titration methods.
Determination of the chiral status of different novel psychoactive substance classes by capillary electrophoresis and β-cyclodextrin derivatives
H?gele, Johannes S.,Hubner, Eva-Maria,Schmid, Martin G.
, p. 1191 - 1207 (2020/07/21)
Besides the abuse of well-known illicit drugs, consumers discovered new synthetic compounds with similar effects but minor alterations in their chemical structure. Originally, these so-called novel psychoactive substances (NPS) have been created to circumvent law of prosecution because of illicit drug abuse. During the past decade, such compounds came up in generations, the most popular compound was a synthetic cathinone derivative named mephedrone. Cathinones are structurally related to amphetamines; to date, more than 120 completely new derivatives have been synthesized and are traded via the Internet. Cathinones possess a chiral center; however, only little is known about the pharmacology of their enantiomers. However, NPS comprise further chiral compound classes such as amphetamine derivatives, ketamines, 2-(aminopropyl)benzofurans, and phenidines. In continuation of our project, a cheap and easy-to-perform chiral capillary zone electrophoresis method for enantioseparation of cathinones presented previously was extended to the aforementioned compound classes. Enantioresolution was achieved by simply adding native β-cyclodextrin, acetyl-β-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin, or carboxymethyl-β-cyclodextrin as chiral selector additives to the background electrolyte. Fifty-one chiral NPS served as analytes mainly purchased from online vendors via the Internet. Using 10 mM of the aforementioned β-cyclodextrins in a 10 mM sodium phosphate buffer (pH 2.5), overall, 50 of 51 NPS were resolved. However, chiral separation ability of the selectors differed depending on the analyte. Additionally, simultaneous enantioseparations, the determination of enantiomeric migration orders of selected analytes, and a repeatability study were performed successfully. It was proven that all separated NPS were traded as racemic mixtures.
Metal-free C-H methylation and acetylation of heteroarenes with PEG-400
Kudale, Vishal Suresh,Wang, Jeh-Jeng
supporting information, p. 3506 - 3511 (2020/06/25)
The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.
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.
Preparation of 4(3H)-quinazolinones from aryldiazonium salt, nitriles and 2-aminobenzoate via a cascade annulation
Ramanathan, Mani,Hsu, Ming-Tsung,Liu, Shiuh-Tzung
, p. 791 - 796 (2019/01/08)
One-pot synthesis of 3-aryl-4(3H)-quinazolinones has been realized through a cascade annulation. Reaction of aryldiazonium salt with a nitrile provides in situ generation of a reactive nitrilium ion, which is attacked by the amino group of 2-aminobenzoate followed by cyclization to deliver the desired product. This strategy offers a convenient and easy access to a wide range of functionalized quinazolinone.
Transition metal-free synthesis of quinazolinones using dimethyl sulfoxide as a synthon
Lee, Seohoo,Sim, Jaeuk,Jo, Hyeju,Viji, Mayavan,Srinu, Lanka,Lee, Kiho,Lee, Heesoon,Manjunatha, Vishwanath,Jung, Jae-Kyung
supporting information, p. 8067 - 8070 (2019/09/19)
Biologically important quinazolinones have been synthesized from 2-aminobenzamides and DMSO. The key feature of the reaction is the utilization of DMSO as a methine source for intramolecular oxidative annulation. The CNS depressant drug methaqualone has also been synthesized by our methodology. The present method involves the synthesis of quinazolinones with a broad substrate scope and a good yield.
Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation
Peng, Jin-Bao,Geng, Hui-Qing,Wang, Wei,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
, p. 10 - 13 (2018/07/03)
A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted both as a solid CO source and a reductant. Notably, methaqualone as a sedative and hypnotic medication can be prepared easily in 68% yield (4b) under our conditions as well.
One-pot synthesis method of quinazolinone compound
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Paragraph 0027; 0029; 0030; 0032; 0034; 0037; 0038, (2018/11/27)
The invention relates to the technical field of chemical synthesis and especially relates to a one-pot synthesis method of a quinazolinone compound, which includes the steps of: (1) with an alcohol, represented as the formula (I), as a raw material, performing a reaction under effect of a photosensitizer in the conditions of light irradiation, gas and room temperature in a solvent to generate an aldehyde represented as the formula (II); (2), with the aldehyde (II) and an o-aminobenzamide derivative represented as the formula (III) as raw materials, performing a reaction under effect of the photosensitizer and an acidic compound in the conditions of light irradiation, gas and room temperature in a solvent to generate a quinazolinone compound represented as the formula (IV). The method is used for synthesizing the quinazolinone compound through a one-pot process. The method is simple in process and employs simple and accessible raw materials, is free of metal catalyst, is carried out through room-temperature reactions with green photocatalysts, is free of peroxides, is low in raw material cost, is high in yield, and is energy-saving and environment-friendly.
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 0064-0067, (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.