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Synthesis and anion recognition studies of new ureylbenzamide-based receptors
A new group of ureylbenzamide-based receptors (1–4) has been synthesized; its binding affinity and capacity to form supramolecular complexes in solution with different anions have been investigated. For designing these receptors, it was considered a combination of the positions of the urea and amide groups (ortho and meta), and the chromophore groups naphthyl and nitrophenyl, yielding four receptors. The position and chromophore structure affected the acidity of the urea and amide hydrogens in the order 4>3>2>1. All the spectroscopic studies showed a significant change of 1 and 2 compared with 3 and 4 in the presence of different TBAX salts in acetonitrile. The 1H-NMR spectra show a preferential interaction of the anions with the urea group in receptors 1 and 2 due to the less steric hindrance, while there is a cooperative interaction of amide group in receptors 3 and 4 due to the closeness of both groups.
Moreno-Valle, Bibiana,Aguilar-Martínez, Milagros,Ochoa-Terán, Adrián,Martínez-Quiroz, Marisela,Miranda-Soto, Valentín,García-Elías, José,Ochoa-Lara, Karen,Labastida-Galván, Victoria,Ordo?ez, Mario
p. 9 - 19
(2018)
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UV-Light-Induced Dehydrogenative N -Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides
A simple, mild, green, and efficient method for the synthesis of 2-aminobenzamides is highly desirable. Herein, we report the development of an efficient, one-pot strategy starting from 2-aminobenzaldehydes and amines with acetic acid in ethyl acetate/acetone using irradiation with UV light for the synthesis of 2-aminobenzamides in high yields; 32 examples proceeded successfully by this photo-induced protocol in up to 92% yield. The reaction was also readily achieved on a gram scale. The utility of the 2-aminobenzamide building block in organic synthesis was shown by their use in the preparation of quinazolinone derivatives. The method was applied to amino acid derivatives as the amine component, which smoothly gave N-(2-aminobenzoyl)acetate derivatives at room temperature. Finally, a plausible mechanism is proposed.
Deng, Wei,Kambe, Nobuaki,Qiu, Renhua,Tang, Niu,Xiang, Jiannan,Yang, Tianbao,Yin, Shuang-Feng,Zeng, Dishu
supporting information

(2022/03/17)

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts
A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.
Faggyas, Réka J.,McGrory, Rochelle,Sutherland, Andrew
supporting information
p. 6127 - 6140
(2021/07/21)

Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic
A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 μM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 μM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated.
Sherafati, Maedeh,Mirzazadeh, Roghieh,Barzegari, Ebrahim,Mohammadi-Khanaposhtani, Maryam,Azizian, Homa,Sadegh Asgari, Mohammad,Hosseini, Samanesadat,Zabihi, Ebrahim,Mojtabavi, Somayeh,Ali Faramarzi, Mohammad,Mahdavi, Mohammad,Larijani, Bagher,Rastegar, Hossein,Hamedifar, Haleh,Hamed Hajimiri, Mir
(2021/02/26)

Efficient synthesis of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives catalyzed by functionalized nanoporous silica
An efficient and facile method has been developed for the synthesis of various 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives, via a three-component reaction of 2-amino-N-(R)-benzamide derivatives with 2-formylbenzoic acid using sulfonic acid functionalized nanoporous silica as an efficient catalyst in ethanol under reflux. High yield of the desired products, reusability of the catalyst, and effortless workup step without using chromatography are the advantages of this method. Graphic abstract: [Figure not available: see fulltext.]
Rayatzadeh, Ayeh,Haghipour, Sirous
p. 103 - 107
(2021/02/05)

Palladium-catalyzed atroposelective coupling-cyclization of 2-isocyanobenzamides to construct axially chiral 2-aryl- And 2,3-diarylquinazolinones
A palladium-catalyzed imidoylative cycloamidation of N-alkyl-2-isocyanobenzamides with 2,6-disubstituted aryl iodides, affording unprecedented axially chiral 2-arylquinazolinones, has been developed with good yields and atroposelectivities. In this coupling-cyclization process, the biaryl linkage and the heteroaromatic ring are formed sequentially in one step. When N-(2,4dimethoxyphenyl)-2-isocyanobenzamide is applied as a substrate, 2,3-diarylquinazolinones containing two stereogenic axes are produced with moderate diastereoselectivity and good enantioselectivities.
Teng, Fan,Yu, Ting,Peng, Yan,Hu, Weiming,Hu, Huaanzi,He, Yimiao,Luo, Shuang,Zhu, Qiang
supporting information
p. 2722 - 2728
(2021/03/01)

Palladium-catalyzed synthesis of novel trifluoromethylated quinazolinone, N-arylquinazoline and N-benzylquinazoline derivatives
A simple and palladium-catalyzed procedure for synthesis of a novel series of potentially biologically active trifluoromethyl-substituted quinazolinones and N-arylquinazoline derivatives via condensation-cyclization reaction of 2-aminobenzamide, 2-amino-N′-arylbenzimidamides and 2-amino-N′-benzylbenzimidamides with trifluoroacetimidoyl chlorides has been developed. noteworthy, this investigation showed the possible of transition-metal-catalyzed activation of trifluoroacetimidoyl chlorides as a carbon trifluoromethylated source for the synthesis of quinazolines and quinazolinone derivatives in good to excellent yields.
Sajadi, Mahdieh Sadat,Kazemi, Elham,Darehkordi, Ali
supporting information

(2021/04/23)

Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives
A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.
Ansari, Samira,Asgari, Mohammad Sadegh,Biglar, Mahmood,Esfahani, Ensieh Nasli,Hamedifar, Haleh,Larijani, Bagher,Mahdavi, Mohammad,Mohammadi-Khanaposhtani, Maryam,Rastegar, Hossein,Tas, Recep,Taslimi, Parham
(2021/07/08)

Efficient one-pot tandem synthesis and cytotoxicity evaluation of 2,3-disubstituted quinazolin-4(3H)-one derivatives
Twenty 2,3-disubstituted quinazolin-4(3H)-one derivatives 1–20 were successfully synthesized in moderate to good yields (25–82%). Their syntheses were based on a one pot tandem ring opening procedure followed by iodine-catalyzed oxidative cyclization of isatoic anhydride with aldehydes, using water as the only solvent under both classical and microwave irradiation conditions. Cytotoxicity assays of the prepared compounds against three human cancer cell lines (HeLa, MCF-7, and A549) indicated that 2, 3, and 20 possessed moderate activities against MCF-7 cells (IC50 = 47.2 μM, 43.9 μM, and 44.9 μM, respectively). Good cytotoxic activities against A549 cells were observed for 3 and 8 with IC50 values of 30.7 μM and 29.8 μM, respectively, which were comparable to the positive control, 5-fluorouracil (5-FU, IC50 = 27.9 μM). Furthermore, compound 4 exhibited slightly stronger activity (IC50 = 23.6 μM) than the positive control 5-FU against the A549 cell line.
Bui, Hue Thi Buu,Do, Kiep Minh,Nguyen, Huy Tran Duc,Mai, Hieu Van,Danh, Thanh La Duc,Tran, De Quang,Morita, Hiroyuki
supporting information

(2021/09/08)

Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one
Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.
Liu, Mingzhu,Wei, Yu,Xu, Liang
supporting information

(2021/10/06)

N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones
N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.
Ding, Chengcheng,Li, Shichen,Ma, Chen,Ren, Jianing,Wang, Yishou
p. 16848 - 16857
(2021/12/06)

Regioselective Br?nsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones
A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N′-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one in good to excellent yield with complete regioselectivity. This protocol tolerates a great variety of functional groups and thus provides a simple and step-efficient method for pyrroloquinazolinone synthesis.
Banerjee, Prabal,Kaur, Navpreet,Singh, Priyanka
p. 3393 - 3406
(2020/03/23)

Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
supporting information
p. 5435 - 5441
(2020/08/03)

Synthesis, Evaluation and Proposed Binding Pose of Substituted Spiro-Oxindole Dihydroquinazolinones as IRAP Inhibitors
Insulin-regulated aminopeptidase (IRAP) is a new potential macromolecular target for drugs aimed for treatment of cognitive disorders. Inhibition of IRAP by angiotensin IV (Ang IV) improves the memory and learning in rats. The majority of the known IRAP inhibitors are peptidic in character and suffer from poor pharmacokinetic properties. Herein, we present a series of small non-peptide IRAP inhibitors derived from a spiro-oxindole dihydroquinazolinone screening hit (pIC50 5.8). The compounds were synthesized either by a simple microwave (MW)-promoted three-component reaction, or by a two-step one-pot procedure. For decoration of the oxindole ring system, rapid MW-assisted Suzuki-Miyaura cross-couplings (1 min) were performed. A small improvement of potency (pIC50 6.6 for the most potent compound) and an increased solubility could be achieved. As deduced from computational modelling and MD simulations it is proposed that the S-configuration of the spiro-oxindole dihydroquinazolinones accounts for the inhibition of IRAP.
?qvist, Johan,Agalo, Faith,Engen, Karin,Gutiérrez-de-Terán, Hugo,Hallberg, Mathias,Jensen, Annika Jenmalm,Konda, Vivek,Larhed, Mats,Lundb?ck, Thomas,Rosenstr?m, Ulrika,Vanga, Sudarsana Reddy
p. 325 - 337
(2020/04/07)

A novel approach for the synthesis of functionalized hydroxylamino derivative of dihydroquinazolinones
A new metal-free and modular approach for the synthesis of various functionalized dihydroquinazolinones has been developed from isatoic anhydride, amines, 4-chloro-N-hydroxybenzimidoylchloride to yield up to 71%. The reaction has been screened in various bases, solvents at different temperatures. The substrate scope of the reaction has been studied with various amines and the possible reaction mechanism for this reaction has also been proposed.
Jaganmohan, Chikkanti,Vinay Kumar,Venkateshwarlu,Mohanty, Sandeep,Kumar, Jaydeep,Venkateswara Rao,Raghunadh, Akula,Tadiparthi, Krishnaji
supporting information
p. 2163 - 2170
(2020/06/10)

Synthesis and biological evaluation of quinoline-quinazolinones for antimicrobial and antileishmanial potential
In an attempt to find a new class of antimicrobial and antileishmanial agents, a series of twenty-three quinoline-quinazolinones were prepared via reaction of 8-hydroxy/methoxyquinoline-2-carbaldehyde with various substituted aminobenzamides. These compounds were screened for their antimicrobial activity against Gram-positive bacteria (B. subtilis), Gram-negative bacteria (E. coli and P. putida) and fungus (C. viswanathii) and antileishmanial activity against promastigotes of L. donovani. Compound 28k exhibited highest activity against B. subtilis with an IC50 of 0.17±0.07 M while compound 28j exhibited highest activity against promastigotes of L. donovani with an IC50 of 6±0.0 M.
Tiwari, Shweta,Kirar, Seema,Banerjee, Uttam Chand,Babu, Neerupudi Kishore,Singh, Sushma,Singh, Inder Pal
p. 1251 - 1258
(2020/12/04)

Method for reducing aromatic nitro into arylamine
The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.
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Paragraph 0177-0180

(2020/07/15)

Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines
Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.
Patel, Khushbu P.,Gayakwad, Eknath M.,Shankarling, Ganapati S.
p. 2661 - 2668
(2020/02/20)

Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
p. 3160 - 3170
(2019/08/07)

Sustainable methine sources for the synthesis of heterocycles under metal- and peroxide-free conditions
Alcohols and ethers were identified as sustainable methine sources for synthesizing quinazolinone and benzimidazole derivatives using a combination of TsOH·H2O/O2 and appropriate bis-nucleophiles for the first time. Deuterium labeling studies clearly proved that the C2 hydrogen of the synthesized heterocycles came from the methine source. These unique reaction conditions were successfully applied to the synthesis of echinozolinone (2e′), 2f′ (a common precursor of rutaecarpine and (±) evodiamine), and dimedazole (6d). Notable features of this method include its low toxicity, use of commercial feedstocks as substrates, low cost, broad functional group tolerance and suitability for a wide range of bis-nucleophilic starting materials.
Senadi, Gopal Chandru,Kudale, Vishal Suresh,Wang, Jeh-Jeng
supporting information
p. 979 - 985
(2019/03/12)

Sulfur-Promoted Synthesis of 2-Aroylquinazolin-4(3H)-ones by Oxidative Condensation of Anthranilamide and Acetophenones
A sulfur-promoted three-component reaction of isatoic anhydride, primary aliphatic or aromatic amines, and acetophenones leading to densely substituted 3-substituted 2-aroylquinazolin-4(3H)-ones is reported. The key step involves a cascade reaction of selective oxidation of the methyl group of the acetophenones, followed by a condensation with anthranilamides. The scope of the reaction is applicable to the synthesis of tryptanthrin and various 3-unsubstituted 2-aroylquinazolin-4(3H)-ones. (Figure presented.).
Nguyen, Thanh Binh,Hou, Jing-ya,Retailleau, Pascal
p. 3337 - 3341
(2019/06/13)

One-Pot, Multistep Reactions for the Modular Synthesis of N, N′-Diarylindazol-3-ones
The pot-economic synthesis of N,N′-diarylindazol-3-ones has been developed using readily available isatoic anhydrides, aryl amines, and aryl boronic acids. A Cu-catalyzed oxidative C-N cross-coupling and dehydrogenative N-N formation sequence under an air atmosphere affords indazol-3-one derivatives in good to excellent yields. Such process merges well with the preceding decarboxylative amination reaction, resulting in a more modular and straightforward approach.
Liu, Shuai,Xu, Liang,Wei, Yu
p. 1596 - 1604
(2019/02/07)

Thermo-Promoted Reactions of Anthranils with Carboxylic Acids, Amines, Phenols, and Malononitrile under Catalyst-Free Conditions
A convenient and atom-economical procedure for the thermo-promoted reactions of anthranil with different substrates was developed. The catalyst-free process affords various useful building blocks with good to moderate yields. This chemistry enables several step- and cost-effective approaches for biologically interesting molecules and provides an efficient platform for the investigation of untapped reactions at high temperature.
Jiang, Jing,Cai, Xin,Hu, Yanwei,Liu, Xuejun,Chen, Xiaodong,Wang, Shun-Yi,Zhang, Yinan,Zhang, Shilei
p. 2022 - 2031
(2019/05/16)

Eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by FeCl3/Al2O3 and analysis of large1H NMR diastereotopic effect
In the present study, we have carried out a condensation reaction for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-amino-N-benzylbenzamide and different aromatic aldehydes using FeCl3 catalyst supported on Al2O3. It was demonstrated that this material can be used successfully for the nucleation of quinazolinones with good to excellent yield; furthermore, the FeCl3/Al2O3 catalyst can be recovered and reused. This catalyst was used before in the synthesis of imidazole with very good yields. The synthesized quinazolinones showed a large range diastereotopic effect over the methylene group and, this anomalous difference was studied through nuclear magnetic resonance (NMR) and computational calculations.
Monreal, Isabel,Sánchez-Castellanos, Mariano,Ramírez-Gualito, Karla,Cuevas, Gabriel,Espinoza, Karla A.,Rivero, Ignacio A.
p. 124 - 131
(2018/12/13)

De novo synthesis of 2,2-bis(dimethylamino)-3-alkyl or benzyl 2,3-dihydroquinazolin-4(1H)-one compounds
A new versatile and efficient strategy for the synthesis of 2,2-bis(dimethylamino)-3-alkyl or benzyl 2,3-dihydroquinazoline-4(1H)-one compounds has been developed by one-pot multicomponent reaction with isatoic anhydride, amines followed by in situ-generated Vilsmeier reagent. The reaction has also been studied with different amines and solvents.
Jaganmohan, Chikkanti,Vinay Kumar,Sandeep Reddy,Mohanty, Sandeep,Kumar, Jaydeep,Venkateswara, Rao,Tadiparthi, Krishnaji,Raghunadh, Akula
supporting information
p. 168 - 174
(2018/01/01)

Copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-ones from benzyl-substituted anthranilamides
An efficient, practical approach to the copper-catalyzed synthesis of 2,3-disubstituted quinazolin-4(3H)-one derivatives is described. The preparation involves treatment of benzyl amines with benzyl anthranilamides in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide (TBAB).
Foroumadi, Parham,Lotfi, Vahid,Mahdavi, Mohammad,Moghimi, Setareh,Soheilizad, Mehdi,Kianmehr, Ebrahim,Firoozpour, Loghman,Asadipour, Ali,Foroumadi, Alireza
p. 267 - 271
(2018/10/15)

Ionic liquid supported on magnetic nanoparticles as a novel reusable nanocatalyst for the efficient synthesis of tetracyclic quinazoline compounds
A magnetic ionic liquid supported on γ-Fe2O3 nanocatalyst was synthesized successfully and characterized by Fourier transform infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, differential scanning calorimetry, X-ray diffraction and scanning electron microscopy. The resulting nano-Fe3O4-supported, ionic liquid was an efficient catalyst for preparation of a series of tetracyclic quinazoline compounds by three components reaction of a mixture of isatoic anhydride and amine with ninhydrin in PEG and the desired products were obtained in good to excellent yields. High efficiency, waste-free, mild reaction conditions, effortless magnetic recovery and reusability up to four continuous cycles are the noteworthy features of the currently employed heterogeneous catalytic system.
Ghorbani-Choghamarani, Arash,Taherinia, Zahra,Nikoorazm, Mohsen
p. 6591 - 6604
(2018/07/03)

Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones
A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.
Qian, Chun,Liu, Kui,Tao, Shou-Wei,Zhang, Fang-Ling,Zhu, Yong-Ming,Yang, Shi-Lin
p. 9201 - 9209
(2018/07/13)

Cu-catalyzed reduction of azaarenes and nitroaromatics with diboronic acid as reductant
A ligand-free copper-catalyzed reduction of azaarenes with diboronic acid as reductant in an aprotic solvent under mild conditions has been developed. Most interestingly, the nitroazaarenes could be reduced exclusively to give the corresponding amines without touching the azaarene moieties. Furthermore, the reductive amination of aromatic nitro compounds and aromatic aldehydes has also been realized. A series of hydrogenated azaarenes and secondary amines were obtained with good functional group tolerance.
Pi, Danwei,Zhou, Haifeng,Zhou, Yanmei,Liu, Qixing,He, Renke,Shen, Guanshuo,Uozumi, Yasuhiro
p. 2121 - 2129
(2018/03/23)

Synthesis and cytotoxicity of novel thioxo-quinazolino[3,4-a]quinazolinones
Various thioxo-quinazolino[3,4-a]quinazolinones were prepared and evaluated for their cytotoxicity in MOLT-4 (lymphoblastic leukemia) and MCF-7 (breast adenocarcinoma) cell lines. Synthesis of the target compounds was started from isatoic anhydride. Successive reaction of isatoic anhydride with benzylamine and 2-nitrobenzaldehyde, reduction of the nitro group, and reaction with CS2 gave 12-benzyl-6-thioxo-6,7,11b,12-tetrahydro-13H-quinazolino[3,4-a]quinazolin-13-one. The latter compound reacted with various 2-chloro-N-substituted acetamides to afford the corresponding fused quinazolinone derivatives.
Mohammadhosseini, Negar,Saeedi, Mina,Moradi, Shahram,Mahdavi, Mohammad,Firuzi, Omidreza,Foroumadi, Alireza,Shafiee, Abbas
p. 125 - 134
(2017/03/14)

Synthesis of 2-(1,2,3-Triazolyl)benzamide Derivatives by a Copper(I)-Catalyzed Multicomponent Reaction
The copper-catalyzed multicomponent reaction of 2-iodobenzamides, NaN3, and terminal alkynes for the synthesis of 2-(1,2,3-triazolyl)benzamide derivatives was achieved in a one-step process over a short period of time under mild conditions. The transformation involved a C(aryl)–N bond formation process followed by an azide–alkyne cycloadditon reaction. The absence of external base was crucial for the preferred reaction pathway to occur.
Hayeebueraheng, Abdulhakim,Kaewmee, Benyapa,Rukachaisirikul, Vatcharin,Kaeobamrung, Juthanat
p. 6714 - 6721
(2017/12/07)

Synthesis and properties of 1,2-dihydro-4(3H)-quinazolinones
We modified the preparative-scale method for the synthesis of 2-aryl 1,2-dihydro-4(3H)-quinazolinone derivatives obtained in high yields by the reaction of new and commercially available aromatic aldehydes with anthranilic acid amides. A series of quinazolinone derivatives possessing anticancer and antiparasitic activities, as well as capable of preventing the progress of neurodegenerative diseases were characterized. There are grounds for clinical trials of these substances in order to select compounds being promising for clinical application.
Khachatryan,Belus,Misyurin,Baryshnikova,Kolotaev,Matevosyan
p. 1044 - 1058
(2017/10/31)

Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid
An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.
Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Pi, Danwei,Shen, Guanshuo
p. 3898 - 3904
(2017/06/13)

An efficient metal-free synthesis of 2-amino-substituted-4(3H)-quinazolinones
2-Amino-substituted-4(3H)-quinazolinones have been synthesized via an efficient metal-free reaction between 2-aminobenzamide derivatives and carbonimidic dibromides. The reaction proceeds in the presence of K2CO3 affording cyclized products in good to excellent yields.
Mirza, Behrooz
p. 146 - 147
(2015/12/23)

An efficient four-step approach toward fused triazino[1,6-a] quinazolines
Herein, we describe a simple, four-step process for the preparation of 1,2,3-triazino[1,6-a]quinazolin-13-ones. This method involves ring-opening, quinazoline-forming condensation, reduction, diazotization accompanied by rapid intramolecular cyclization in the last step afforded the desired products with structurally complex heterocyclic core in excellent to high yields.
Sayahi, Mohammad Hosein,Baghersaei, Shirin,Goli, Fereshteh,Moghimi, Setareh,Mahdavi, Mohammad,Firoozpour, Loghman,Shafiee, Abbas,Foroumadi, Alireza
p. 189 - 192
(2016/05/09)

Reaction of benzyl alcohols, isatoic anhydride, and primary amines mediated by I2/K2CO3 in water: A new and green approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
An efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones proceeding via a three-component reaction between benzyl alcohols, isatoic anhydride, and primary amines in the presence of iodine and potassium carbonate is reported. This protocol allows the straightforward preparation of the titled products using readily available benzyl alcohols instead of unstable aldehydes under mild oxidative conditions.
Azimi, Seyedeh Bahareh,Azizian, Javad
p. 181 - 184
(2015/12/30)

Unusual Acid- and Base-Catalyzed C-N Bond Formation Approach through Reaction of Chromonyl Meldrum's Acid and Nitrogen Binucleophiles
Reaction of chromonyl Meldrum's acid and N-substituted 2-aminobenzamides was studied in the presence of acidic and basic catalysts. The use of methanesulfonic acid as a catalyst in this reaction led to the synthesis of chromonyl quinazolinones through employing Meldrum's acid as a carbon leaving group. However, in the presence of basic catalyst, this reaction gave functionalized 2-pyridones.
Balalaie, Saeed,Bijanzadeh, Hamid Reza,Mehrparvar, Saber,Rominger, Frank
supporting information
p. 782 - 788
(2016/03/09)

CuBr/Et3N-Promoted Reactions of 2-Aminobenzamides and Isothiocyanates: Efficient Synthesis of Novel Quinazolin-4(3H)-ones
A series of novel quinazolin-4(3H)-one derivatives were efficiently synthesized starting from isatoic anhydride. First, reaction of isatoic anhydride and amines in H2O at room temperature afforded 2-aminobenzamides. Then, CuBr/Et3N promoted reaction of 2-aminobenzamides and different aryl isothiocyanates in DMF at 80° afforded the title compounds in good yield.
Mahdavi, Mohammad,Asadi, Mehdi,Khoshbakht, Mahsa,Saeedi, Mina,Bayat, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
p. 378 - 383
(2016/06/01)

Bridgehead Bicyclo[4.4.0]boron Heterocycles: A One-Pot Four-Component Synthesis of Dibenzo[e,i][1,3,7,2]oxadiazaborecin-8(7H)-ones
A one-pot four-component synthesis of 6-aryl-6H-dibenzo[e,i][1,3,7,2]oxadiazaborecin-8(7H)-ones is described. Heating a mixture of isatoic anhydride and a benzylamine afforded the corresponding anthranilamide derivative, which was condensed with a 2-hydroxybenzaldehyde and an arylboronic acid under solvent-free conditions to produce bridgehead bicyclo[4.4.0]-boron heterocycles in good to excellent yields. Single-crystal X-ray analysis conclusively confirms the structures of the obtained bridgehead bicyclic 6–6 heterocyclic compounds.
Adib, Mehdi,Shabanibalajadeh, Sadegh,Sheikhi, Ehsan,Rahimi-Nasrabadi, Mehdi,Zhu, Long-Guan
p. 659 - 664
(2016/09/21)

Synthesis of novel 1,2,3-triazole derivatives of 2,3-dihydroquinazolin-4(1H)-one
Abstract: This work reports an efficient route for the synthesis of novel 1,2,3-triazole derivatives of 2,3-dihydroquinazolin-4(1H)-one starting from isatoic anhydride via a three-step reaction. The resulting 2-amino-N-substituted benzamides from the reaction of isatoic anhydride and benzylamines underwent coupling cyclization reaction with 4-(prop-2-yn-1-yloxy)benzaldehyde, and then click reaction with in situ prepared organic azides afforded the title compounds in good yields. Graphical abstract: [Figure not available: see fulltext.]
Mahdavi, Mohammad,Saeedi, Mina,Karimi, Maryam,Foroughi, Niloufar,Hasanshahi, Fatemeh,Alinezhad, Heshmatollah,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
p. 2151 - 2156
(2016/11/17)

Mechanistic insights into a catalyst-free method to construct quinazolinones through multiple oxidative cyclization
A novel one-pot benign oxidative cyclization of alcohols with 2-aminobenzamides was successfully developed without catalyst to afford the quinazolinones under O2. This one-pot protocol involved oxidations and cyclizations to construct the skeleton of quinazolinones through possibly three kinds of distinct reaction mechanisms.
Wang, Zhen-Zhen,Tang, Yu
p. 1330 - 1336
(2017/02/15)

Synthesis of 2,3-Disubstituted Quinazolinone Derivatives through Copper Catalyzed C-H Amidation Reactions
The synthesis of quinazolinone derivatives was achieved from 2-iodobenzamide derivatives and various benzylamines, allylamine, and cinnamylamine derivatives through a one-pot copper-catalyzed reaction. In this reaction, the amine component (benzylamine/allylamine/cinnamylamine) is N-arylated with 2-iodobenzamide derivatives through Ullman coupling, followed by an intramolecular C-H amidation in the presence of copper catalyst. Copper-catalyzed tandem-Ullman N-alkylation and intramolecular C-H amidation reaction protocol for the synthesis of 2-phenylquinazolinone and quinazolinone derivatives from N-substituted 2-iodo-benzamides and benzylamines, allyl, and cinnamylamine is achieved.
Kotipalli, Trimurtulu,Kavala, Veerababurao,Janreddy, Donala,Bandi, Vijayalakshmi,Kuo, Chun-Wei,Yao, Ching-Fa
p. 1182 - 1193
(2016/03/05)

Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones
A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.
Bao, Yajie,Yan, Yizhe,Xu, Kun,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
p. 4736 - 4742
(2015/05/13)

I2-catalyzed aerobic oxidative C(sp3)-H amination/C-N cleavage of tertiary amine: Synthesis of quinazolines and quinazolinones
An iodine-catalyzed oxidative C(sp3)-H amination/C-N cleavage of tertiary amines couducted under an oxygen atmosphere has been developed and affords a route to quinazolines and quinazolinones in good to excellent yields via a domino ring annulation. The method is metal-free, peroxide-free, and operationally simple to implement with a wide scope of substrates and represents a new avenue for multiple C-N bond formations.
Yan, Yizhe,Xu, Ying,Niu, Bin,Xie, Huifang,Liu, Yanqi
p. 5581 - 5587
(2015/06/16)

Synthesis of furyl-, furylvinyl-, thienyl-, pyrrolinylquinazolines and isoindolo[2,1-a]quinazolines
A method for the synthesis of hydrogenated furyl-, furylvinyl-, thienyl-, and pyrrolinyl-substituted quinazolin-4-ones was developed. A possibility of the reaction of 2-furylquinazolines with maleic anhydride was demonstrated. A number of quinazolines obtained were subjected to a primary bioscreening on inhibition of acetylcholinesterase.
Zaytsev,Revutskaya,Ku?menko,Novikov,Zubkov,Sorokina,Nikitina,Toze,Varlamov
p. 1345 - 1353
(2016/03/08)

Novel β-carboline-quinazolinone hybrid as an inhibitor of Leishmania donovani trypanothione reductase: Synthesis, molecular docking and bioevaluation
Trypanothione reductase (TR) is a vital enzyme in the trypanothione based redox metabolism of trypanosomatid parasites. It is one of the few chemically validated targets for Leishmania. Herein, we report the synthesis of novel β-carboline-quinazolinone hybrids that are able to inhibit Leishmania donovani TR (LdTR) and subsequently inhibit cell growth. A molecular modeling approach based on docking studies and subsequent binding free energy estimation was performed in the active site of LdTR to understand their possible binding sites. With the enzymatic assay on LdTR with compounds, we were able to identify six hit compounds (8j-8o) that were all found to be the competitive inhibitors of TR with Ki in the range of 0.8-9.2 μM. The whole-cell screening assay highlighted the analogues 8k, 8l and 8n as the most active compounds with IC50 of 4.4, 6.0 and 4.3 μM, respectively, along with an adequate selectivity index (SI) of >91, 36 and 24, respectively. This journal is
Chauhan, Shikha S.,Pandey, Shashi,Shivahare, Rahul,Ramalingam, Karthik,Krishna, Shagun,Vishwakarma, Preeti,Siddiqi,Gupta, Suman,Goyal, Neena,Chauhan, Prem M. S.
p. 351 - 356
(2015/03/18)

Synthesis and anticancer activity of N -substituted 2-arylquinazolinones bearing trans -stilbene scaffold
A novel series of 2-arylquinazolinones 7a-o bearing trans-stilbene moiety were designed, synthesized, and evaluated against human breast cancer cell lines including human breast adenocarcinoma (MCF-7 and MDA-MB-231) and human ductal breast epithelial tumor (T-47D). Among the tested compounds, the sec-butyl derivative 7h showed the best profile of activity (IC50 5 μM) against all cell lines, being 2-fold more potent than standard drug, etoposide. Our investigation revealed that the cytotoxic activity was significantly affected by N3-alkyl substituents. Furthermore, the morphological analysis by acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that the prototype compound 7h can induce apoptosis in MCF-7 and MDA-MB-231 cells.
Mahdavi, Mohammad,Pedrood, Keyvan,Safavi, Maliheh,Saeedi, Mina,Pordeli, Mahboobeh,Ardestani, Sussan Kabudanian,Emami, Saeed,Adib, Mehdi,Foroumadi, Alireza,Shafiee, Abbas
p. 492 - 499
(2015/04/14)

Solvent-free synthesis of novel benzodiazepine derivatives by a three-component base-catalysed reaction of isatoic anhydride, a primary amine and chloroacetyl chloride
Heating isatoic anhydride with a series of primary amines at 150 °C under solvent-free conditions yielded 2-amino-N-alkylbenzamides which, in the same pot, reacted readily with chloroacetyl chloride in the presence of poly(dimethylaminoethyl acrylamide)-modified magnetic nanoparticles (MNP@PDMA), a base catalyst, to give 4-alkyl-1,4-benzodiazepine-2,5-diones in good yields without formation of by-products.
Seydey, Mohsen Khalilpour,Rezaei, Zahra,Homami, Seyed Saied
p. 286 - 288
(2015/06/02)

An efficient one pot synthesis of 2-amino quinazolin-4(3H)-one derivative via MCR strategy
A novel multi-component reaction strategy was developed for the construction of important building blocks, 2-amino 3-substituted quinazolinone derivatives from isatoic anhydride and amine with electrophilic cyanating compound, N-cyano-4-methyl-N-phenylbenzenesulfonamide (NCTS). The quinazolinone synthesis proceeds via a sequential series of reactions such as nucleophilic attack of the amine group on the carbonyl group of isatoic anhydride followed ring opening and subsequent decarboxylation, nucleophilic attack of amine to nitrile, followed by heterocyclization.
Narayana Murthy,Nikumbh, Satish P.,Praveen Kumar,Vaikunta Rao,Raghunadh, Akula
supporting information
p. 5767 - 5770
(2015/09/29)

Novel 1,2,3,4-Tetrahydroquinazolinones via Reaction of 2-Amino-N-substituted Benzamides and Dimethyl Acetylenedicarboxylate
Reaction of 2-amino-N-substituted benzamides and dimethyl acetylenedicarboxylate (DMAD) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in H2O at room temperature led to the formation of novel 1,2,3,4-tetrahydroquinazolinones.
Nahavandian, Semiramis,Allameh, Sadegh,Saeedi, Mina,Ansari, Shirin,Mahdavi, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
p. 1028 - 1033
(2015/11/23)