5943-92-0Relevant academic research and scientific papers
Catalytic formation of N3-substituted quinazoline-2,4(1: H,3 H)-diones by Pd(ii)EN?GO composite and its mechanistic investigations through DFT calculations
Biswas, Surajit,Dolai, Malay,Haque Biswas, Imdadul,Haque, Najirul,Islam, Md Sarikul,Islam, Sk Manirul,Khatun, Resmin,Sengupta, Manideepa
, p. 141 - 151 (2020)
In the current era, the scientific community is very much interested to utilize the greenhouse gas, carbon dioxide, through chemical fixation in order to produce value-based fine organic chemicals. The chemical combination of atmospheric carbon dioxide, isocyanides, and 2-iodoaniline in a one-pot reaction for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives is a straight forward and attractive methodology to avoid multi-step and more toxic reagent containing routes. In this study, a heterogeneous catalyst was designed and synthesized from aminically modified graphene oxide by the incorporation of palladium metal. The catalyst was characterized by FT-IR, XRD, ICP-AES, Raman spectroscopy, XPS, TEM, SEM, EDX, and N2 absorption desorption studies. In this report, the formation of N3-substituted 2,4(1H,3H)-quinazolinediones was performed under mild and heterogeneous reaction conditions under 1 bar CO2 pressure. The catalyst is very efficient to produce the quinazoline derivatives. For the investigation of the mechanistic route of the catalytic reaction, density functional theory (DFT) calculations were also monitored. We have checked the recyclability of the catalyst, the results indicated that the catalyst maintained its catalytic efficacy even after six cycles of use.
Synthesis, biological evaluation and molecular docking of 3-substituted quinazoline-2,4(1H, 3H)-diones
Bastidas, Pedro,Calderón-Zamora, Loranda,García-Páez, Fernando,Ochoa-Terán, Adrián,Osuna-Martínez, Ulises,Picos-Corrales, Lorenzo A,Rendón-Maldonado, Guadalupe,Santos-Ballardo, Lumadhar,Sarmiento-Sánchez, Juan I
, (2020/08/14)
Abstract: The quinazoline-2,4-diones scaffold is found in bioactive compounds, commercial drugs and exhibit important biological activities. However, their antidiabetic activity is rarely explored. For this purpose, an easy one-pot three-components and straightforward synthesis of 3-substituted quinazoline-2,4-diones was designed, in both, the catalyst- and solvent-free conditions under microwave irradiation. Additionally, the synthesized compounds were screened for in vitro α-amylase and α-glucosidase inhibitory activity, as well as antioxidants and cytotoxicity. The quinazoline-2,4-diones were isolated, with yields in the range of 30-65percent. The compounds 3d, 3e, 3g and 3h displayed moderate activity against α-amylase and/or α-glucosidase enzymes compared with the acarbose drug. The molecular docking study revealed that all active compounds displayed a different type of intermolecular interaction in the pocked site of these enzymes. Interestingly, in the Artemia salina assay, the compound 3d exhibited a higher cytotoxic effect than 5-fluorouracil. All these results support the pharmacological potential of quinazoline-2,4-diones since all evaluated compounds behave as moderate inhibitors of the enzymes α-amylase and/or α-glucosidase. Graphic abstract: An easy one-pot three-components and straightforward synthesis of 3-substituted quinazoline-2,4-diones was designed, in both, the catalyst- and solvent-free conditions under microwave irradiation. Moreover, the in vitro α-amylase and α-glucosidase inhibitory activity, as well as antioxidants and cytotoxicity are reported.[Figure not available: see fulltext.]
Iridium-Catalyzed C-H Amination of Weinreb Amides: A Facile Pathway toward Anilines and Quinazolin-2,4-diones
Dong, Xunqing,Ma, Panpan,Zhang, Tao,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian
, p. 13096 - 13107 (2020/11/26)
C-H amination of arenes directed by weakly coordinating Weinreb amides has been achieved with an iridium catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating agent, providing a robust method of producing synthetic useful ortho-TrocNH aryl Weinreb amides. Taking advantage of the reactivity of Weinreb amide and Troc groups in the amination products, selective hydrolysis was achieved as an attractive process for the synthesis of ortho-NH2 aryl Weinreb amides, which are the building blocks useful in the synthesis of bioactive compounds, and cascade aminocyclization with primary amines was successful and provided an efficient pathway for the construction of quinazolin-2,4-diones, which are present in various alkaloids and natural products.
Combining Isocyanides with Carbon Dioxide in Palladium-Catalyzed Heterocycle Synthesis: N3-Substituted Quinazoline-2,4(1H,3H)-diones via a Three-Component Reaction
Mampuys, Pieter,Neumann, Helfried,Sergeyev, Sergey,Orru, Romano V. A.,Jiao, Haijun,Spannenberg, Anke,Maes, Bert U. W.,Beller, Matthias
, p. 5549 - 5556 (2017/08/17)
We report a Pd-catalyzed three-component reaction of 2-bromoanilines, carbon dioxide, and isocyanides. The combination of these two readily available C1-reactants, featuring a huge difference in kinetic and thermodynamic stability, is hitherto unprecedented in transition-metal catalysis. With this one-pot three-component reaction, N3-substituted quinazoline-2,4(1H,3H)-diones are obtained in moderate to high yields in a completely regio- and chemoselective manner. Our approach easily allows variation of the arene and N3-substitution pattern of the desired heterocycle. The formal synthesis of different APIs illustrates its practical applicability. In addition, the methodology also allows for a convenient and selective 13C-labeling through the use of 13CO2. This is illustrated for [2-13C]-2,4-dichloro-6,7-dimethoxyquinazoline synthesis, a key intermediate for several APIs.
Green synthesis of quinazolinone derivatives catalyzed by iodine in ionic liquid
Wang, Shu-Liang,Yang, Ke,Yao, Chang-Sheng,Wang, Xiang-Shan.
experimental part, p. 341 - 349 (2011/11/12)
A series of quinazolinone derivatives were synthesized by the reaction of 2-aminobenzamides and triethyl orthoformate or triphosgene in ionic liquid of [BMIm]BF4 at 80 °C catalyzed by iodine in good yields. Compared to other methods, this new procedure has the advantages of mild reaction conditions, good yields, operational simplicity, and environmentally friendly procedure. Copyright Taylor & Francis Group, LLC.
3-aryl(alkyl)quinazoline-2,4(1H,3H)-diones and their alkyl derivatives
Shestakov,Sidorenko,Bushmarinov,Shikhaliev,Antipin
experimental part, p. 1691 - 1696 (2010/04/29)
Two-stage reaction of methyl anthranilate with aryl(alkyl) isocyanates in keeping with the quantumchemical calculations and XRD analysis resulted in 3-aryl(alkyl)quinazoline-2,4(1H,3H)-diones that by treatment with alkyl halides, phenacyl bromides, esters
Tandem palladium-catalyzed urea arylation-intramolecular ester amidation: Regioselective synthesis of 3-alkylated 2,4-quinazolinediones
Willis, Michael C.,Snell, Robert H.,Fletcher, Anthony J.,Woodward, Robert L.
, p. 5089 - 5091 (2007/10/03)
(Chemical Equation Presented) o-Halo benzoates can be combined with monoalkyl ureas in a tandem palladium-catalyzed arylation-ester amidation sequence to deliver quinazolinedione products. The reactions are regioselective for formation of the 3-N-alkyl isomers. Significant variation of both coupling partners is possible, allowing the synthesis of a diverse array of substituted quinazolinediones, exemplified by the preparation of a simple unsymmetric-dialkylated natural product.
Cyanic Acid Ester. 35. On Formation and Consecutive Reactions of N-Cyanato Phthalimide. New Specifically Activated and Blocked Isatoic Acid Derivatives
Martin, Dieter,Nadolski, Karin,Gruendemann, Egon
, p. 737 - 746 (2007/10/02)
Depending on the reaction conditions N-hydroxy-phthalimide affords on treatment with cyanogen bromide via N-cyanato phthalimide 2 the iminocarbonate 3 and isatoic acid derivatives 7 and 16.Both the latter react with nucleophiles as isatoic acid derivatives activated on the carboxylic group and protected on the carbamic group or vice versa, furnishing N,N-bis alkoxycarbonyl anthranilic acid amides 9, N-alkoxycarbonyl anthranilic acid 12, o-alkoxycarbonyl phenyl ureas 17 and the benzotriazepin-2,5-dione 14.The structures of the new compounds are proved by 1H-n.m.r. and 13C-n.m.r. measurements as well as independent synthesis.
Convenient Preparation of N-substituted 2-Amino-4H-3,1-benzoxazin-4-ones and 3-Substituted 2,4(1H,3H)-Quinazolinediones
Papadopoulos, E. P.,Torres, C. D.
, p. 269 - 272 (2007/10/02)
Room temperature of 2-(3-arylureido)benzoic acids (1) and methyl2-(3-alkyl-, or 3-arylureido)-benzoates (2) with concentrated sulfuric acid leads to N-substituted 2-amino-4H-3,1-benzoxazin-4-ones (3) in generally very good yields.The isomeric 3-substitute
