- β-Alanine-functionalized magnetic graphene oxide quantum dots: an efficient and recyclable heterogeneous basic catalyst for the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione and 2,3-dihydroquinazolin-4(1H)-one derivatives
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In this research, we report a novel synthesis of magnetic β-alanine-functionalized-graphene oxide quantum dots Fe3O4@GOQDs-N-(β-alanine) as a recyclable and eco-friendly heterogeneous nanocatalyst. The catalytic efficiency of these nanosheets was explored as a basic catalyst for a one-pot three-component synthesis of various 1H-pyrazolo[1,2-b]phthalazine-5,10-dione and 2,3-dihydroquinazolin-4(1H)-one derivatives. The reactions proceeded smoothly under mild and green conditions to afford the respected products in excellent yields. The structure of this newly fabricated catalyst was successfully confirmed by different analytical techniques such as Fourier transform infrared spectroscopy, X-ray diffraction, field emission-scanning electron microscopy, high-resolution transmission electron microscopy, energy-dispersive X-ray spectroscopy, vibrating sample magnetometry, and thermogravimetric analysis. The stability and recyclability of the catalyst were examined by performing the model reaction in six consecutive runs. The recovered catalyst from the first run was directly used for the next runs with no significant loss of catalytic activity.
- Khaleghi Abbasabadi, Masoud,Azarifar, Davood
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- Corrigendum to “Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions” [Tetrahedron Lett. 76/27 (2020) 131312] (Tetrahedron (2020) 76(27), (S004040202030466X), (10.1016/j.tet.2020.131312))
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The authors regret the following errors: 1. In page 1, “Additionally, 2,3-dihydroquinazolin-4(1H). -one derivatives can easily…” should be changed to “Additionally, 2,3-dihydroquinazolin-4(1H)-one derivatives can easily…” 2. In page 1, “… numerous protocols have been developed recently for the synthesis using catalysts including acidic reagents [21], [?] [29] lewis acids [30–36],…” should be changed to “… numerous protocols have been developed recently for the synthesis using catalysts including acidic reagents [21–29], lewis acids [30–36],…” 3. In page 1, “… alternative methods to perform organic. synthesis under environmentally benign conditions is in…” should be changed to “… alternative methods to perform organic synthesis under environmentally benign conditions is in…” 4. In page 2, “… condensation, which were. readily available based on our previous publicationsn…” should be changed to “… condensation, which were readily available based on our previous publications…” 5. In page 3, “… while bringing down the catalyst loading to 1 mol % led. to a reduction in the yield to…” should be changed to “… while bringing down the catalyst loading to 1 mol % led to a reduction in the yield to…” 6. In page 3, “… transformation to different substituted isatoic. anhydrides was performed.” should be changed to “… transformation to different substituted isatoic anhydrides was performed.” 7. In page 3, “… easily separated from the. reaction mixture via simple centrifugation…” should be changed to “… easily separated from the reaction mixture via simple centrifugation…” 8. The chemical structure 4a-4g should be changed in Table 2 as below: Table 2. HPAIL catalyzed three-component condensation of isatoic anhydrides, amines and aldehydes (or ketones).a [Figure presented] The authors would like to apologise for any inconvenience caused.
- Cai, Jing,Fu, Renzhong,Liu, Yang,Yang, Yang,Zeng, Xiaojun
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- Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions
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A series of 2,3-dihydroquinazoline-4(1H)-one derivatives have been synthesized via one-pot three-component reaction using isatoic anhydrides, amines and aldehydes (or ketones) catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media and operational simplicity are the main highlights. Furthermore, the catalyst can be recovered and reused without evident loss of reactivity. This method provides a green and much improved protocol over the existing methods.
- Yang, Yang,Fu, Renzhong,Liu, Yang,Cai, Jing,Zeng, Xiaojun
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- Method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone
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The invention discloses a method for selectively synthesizing polysubstituted dihydroquinazolinone or quinazolinone. According to the method, heteropolyacid ion liquid is taken as a catalyst, microwave heating and solvent-free synthesis technologies are utilized, and dihydroquinazolinone and quinazolinone derivatives are selectively synthesized through a 'one-pot-method' synthetic strategy with isatoic anhydride or derivatives of the isatoic anhydride, amine and aldehyde as raw materials. Compared with the prior art, the method has the multiple advantages that the efficiency is high, the costis low, environmental friendliness is realized, reaction selectivity is good, the product yield is high, selective synthesis can be realized, the catalyst is convenient to recover and apply, operationis easy, and industrial mass production is convenient, and the method is an environment-friendly efficient selective synthesis novel method and meets the environment-friendly and chemical developmentidea.
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Paragraph 0074-0077
(2019/11/12)
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- Synthesis, 2D-QSAR studies and biological evaluation of quinazoline derivatives as potent anti-trypanosoma cruzi agents
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Background: Chagas disease affects about 7 million people worldwide. Only two drugs are currently available for the treatment for this parasite disease, namely, benznidazol (Bzn) and nifurtimox (Nfx). Both drugs have limited curative power in the chronic phase of the disease. Therefore, continuous research is an urgent need so as to discover novel therapeutic alternatives. Objective: The development of safer and more efficient therapeutic anti-T. cruzi drugs continues to be a major goal in trypanocidal chemotherapy. Method: Synthesis, 2D-QSAR and drug-like physicochemical properties of a set of quinazolinone and quinazoline derivatives were studied as trypanocidal agents. All compounds were screened in vitro against Trypanosoma cruzi (Tulahuen strain, Tul 2 stock) epimastigotes and bloodstream trypomastigotes. Results: Out of 34 compounds synthesized and tested, six compounds (5a, 5b, 9b, 9h, 13f and 13p) displayed significant activity against both epimastigotes and tripomastigotes, without exerting toxicity on Vero cells. Conclusion: The antiprotozoal activity of these quinazolinone and quinazoline derivatives represents an interesting starting point for a medicinal chemistry program aiming at the development of novel chemotherapies for Chagas disease.
- Battini, Leandro,Bollini, Mariela,Bruno, Ana M.,Casal, Juan J.,Lombardo, María E.,Ni?o, María E.,Puente, Vanesa R.,Sasiambarrena, Leandro D.,Valdez, Damián A. G.
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p. 265 - 276
(2019/07/12)
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- Metal-Free Oxidative C(sp 3)-N Coupling by HBr and DMSO: A Novel Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones
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A metal-free oxidative C(sp 3)-N coupling process has been developed for the synthesis of 2,3-dihydroquinazolin-4(1 H)-ones. The reaction between primary amines, isatoic anhydride, and benzylic alcohols in the presence of HBr in DMSO at 80 °C affords 2,3-dihydroquinazolin-4(1 H)-ones in excellent yields. Under these reaction conditions, benzylic alcohols react with in situ generated bromodimethylsulfonium bromide to form alkoxysulfonium intermediates. These intermediates undergo an oxidative cyclization reaction with primary amines and isatoic anhydride to produce the title products.
- Rezaei, Narjes,Sheikhi, Ehsan,Ranjbar, Parviz Rashidi
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p. 912 - 917
(2018/02/26)
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- Sulfated polyborate: mild, efficient and eco-friendly catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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Abstract: An efficient, inexpensive and recyclable sulfated polyborate catalyst was applied in a three-component, one-pot cyclocondensation of isatoic anhydride, aldehydes and ammonium acetate/amines to afford the corresponding 2,3-dihydroquinazolin-4(1H)-ones. The key advantages of the present method are high yields, short reaction time, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards. Graphical Abstract: [Figure not available: see fulltext.].
- Khatri, Chetan K.,Patil, Manisha S.,Chaturbhuj, Ganesh U.
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p. 1683 - 1689
(2017/06/27)
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- 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
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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
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p. 181 - 184
(2015/12/30)
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- Hydroxyapatite nanoparticles (HAP NPs): A green and efficient heterogeneous catalyst for three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media
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Hydroxyapatite nanoparticles (HAP NPs) are found to be an efficient catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media via a three-component one-pot condensation of isatoic anhydride and aromatic aldehydes with primary amines or ammonium salts. The nanocatalyst (characterized by FT-IR, XRD, SEM-EDS and TEM techniques) is easily recyclable six times without the significant loss of catalytic activity. Other remarkable features include the wide range of functional group tolerance and good to excellent yields of the products under mild reaction conditions.
- Razavi, Nasrin,Akhlaghinia, Batool
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p. 447 - 457
(2016/01/12)
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- Starch solution as an efficient and environment-friendly catalyst for one-pot synthesis of β-aminoketones and 2,3-dihydroquinazolin-4(1H)-ones in EtOH
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An efficient, practical and atom-efficient method has been developed for the preparation of β-aminoketones and 2,3-dihydroquinazoline-4(1H)-ones via multicomponent one-pot reaction in starch solution as an entirely green catalyst. The advantages of this novel protocol are high yields, short reaction time, simple methodology, easy work-up and purification, lack of toxicity and eco-friendly catalyst. Graphical Abstract: [Figure not available: see fulltext.].
- Maghsoodlou, Malek Taher,Khorshidi, Naimeh,Mousavi, Mir Rasul,Hazeri, Nourallah,Habibi-Khorassani, Sayyed Mostafa
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p. 7497 - 7508
(2015/09/29)
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- Pentafluorophenylammonium triflate as a suitable and effective metal-free catalyst for the synthesis of quinazoline derivatives via one-pot multicomponent method
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A simple and facile synthesis of highly functionalized quinazoline derivatives has been successfully developed by treatment of aldehydes, ammonium acetate, and 2-aminoaryl ketones or isatoic anhydride under reflux conditions in the presence of a pentafluorophenylammonium triflate (PFPAT) organocatalyst. These catalytic condensation reactions represent green chemical processes, while the PFPAT organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.
- Khaksar, Samad,Gholami, Milad
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p. 3709 - 3718
(2015/06/08)
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- Powdered diethylaminoethyl cellulose as biomass-derived support for phosphotungstic acid: New solid acidic catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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Finely powdered diethylaminoethyl cellulose is prepared through a bottom-up synthetic method using NaOH/urea aqueous solution as solvent. Phosphotungstic acid anchored on the powdered diethylaminoethyl cellulose can be used as a biopolymer-supported solid acidic catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from isatoic anhydride, amines, and aldehydes. The catalyst could be easily recovered by simple filtration and reused several times with minor decreases in the reaction yields.
- Li, Shaokang,Zhang, Qianqian,Peng, Yanqing
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p. 1859 - 1864
(2015/10/29)
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- New applications of phosphoric acid supported on alumina (H 3PO4-Al2O3) as a reusable heterogeneous catalyst for preparation of 2,3-dihydroquinazoline-4(1H)-ones, 2H-indazolo[2,1-b]phthalazinetriones, and benzo[4,5]imidazo[1,2-a]pyrimidines
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An eco-friendly procedure for synthesis of 2,3-dihydroquinazoline-4(1H)- one, 2H-indazolo[2,1-b]phthalazinetrione, and benzo[4,5]imidazo[1,2-a]pyrimidine derivatives by three-component reaction, with phosphoric acid supported on alumina as catalyst, is described. Noticeable features of the method are that it is solvent-free, work-up is easy, yields are excellent, and the catalyst is reusable.
- Shaterian, Hamid Reza,Fahimi, Nafiseh,Azizi, Kobra
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p. 1879 - 1898
(2014/05/06)
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- Br?nsted acidic ionic liquids catalyze the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives
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A simple and facile method for the green synthesis of 2,3- dihydroquinazolin-4(1H)-one derivatives by direct three-component cyclo-condensation of isatoic anhydride, ammonium acetate (or primary amines), and arylaldehydes using different Br?nsted acidic ionic liquids, for example 2-pyrrolidonium hydrogensulfate ([hnmp][HSO4]), N-methyl-2-pyrrolidonium hydrogensulfate ([NMP][HSO4]), and N-methyl-2-pyrrolidonium dihydrogenphosphate ([NMP][H2PO 4]), as reusable catalysts under solvent-free conditions is described. In addition, reaction of anthranilamide and arylaldehydes for synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives was investigated.
- Shaterian, Hamid Reza,Aghakhanizadeh, Morteza
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p. 1655 - 1668
(2014/05/06)
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- Nano-indium oxide: An efficient catalyst for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones with a greener prospect
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Nano-In2O3 is found to be a remarkable efficient catalyst for the one-pot three-component condensation of isatoic anhydride, primary amine or ammonium salts and aromatic aldehydes for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones in aqueous media. In2O3 nanoparticles are easily recyclable without the significant loss of catalytic activities.
- Santra, Sougata,Rahman, Matiur,Roy, Anupam,Majee, Adinath,Hajra, Alakananda
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- Cation-exchange resin as an efficient hetero- Geneous catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones
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Various mono- and disubstituted 2,3-dihydro-4(1H)-quinazolinones were synthesized efficiently by a one-pot three-component condensation of isatoic anhydride, aromatic aldehydes, and ammonium salts or primary amines using a strong acidic cation-exchange resin as the catalyst in EtOH-H2O solution. The catalyst is cheap, efficient, stable, and reusable under the reaction conditions. The novel method offers several advantages, such as excellent yields, environmentally friendly reaction media, and simple procedure.
- Wang,Zhang,Gao,Liang
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p. 897 - 902
(2013/01/15)
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- Three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in 2,2,2-trifluoroethanol
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Trifluoroethanol (TFE) is found to be an efficient and recyclable medium in promoting one-pot, three-component coupling reactions of isatoic anhydride, aldehyde and ammonium acetate or primary amine to afford the corresponding 2,3-dihydroquinazolin-4(1H)-one derivatives in high yields. The solvent (TFE) can be readily separated from reaction products and recovered in excellent purity for direct reuse.
- Khaksar, Samad,Talesh, Saeed Mohammadzadeh
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p. 779 - 783
(2012/10/30)
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- Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)- ones using copper benzenesulfonate as a reusable catalyst in aqueous solution
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Copper benzenesulfonate was found to be an effective catalyst for one-pot three-component cyclocon-densation of isatoic anhydride, aromatic aldehydes, and ammonium salts or primary amines in aqueous solution to afford the corresponding mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones in good yields. The catalyst is reusable and could be recycled for several times without distinct decrease in its efficiency. Springer-Verlag 2011.
- Wang, Min,Zhang, Ting T.,Liang, Yan,Gao, Jing J.
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experimental part
p. 835 - 839
(2012/07/28)
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- Silica supported zinc (II) chloride (SiO2-ZnCl2) as an efficient catalyst for the eco-friendly synthesis of 2,3-dihydroquinazolin- 4(1 H)-ones
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Silica supported zinc (II) chloride (SiO2-ZnCl2) as an efficient and non-toxic heterogeneous catalyst have been used for the simple and facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones through the direct cyclo-condensation of anthranilamide and aldehydes or one-pot three-component cyclo-condensation of isatoic anhydride, ammonium acetate (or amines) and aldehydes under solvent-free conditions.
- Ghashang, Majid
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p. 1213 - 1218
(2013/02/23)
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- Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)- ones using aluminum methanesulfonate as a reusable catalyst
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A wide range of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones were synthesized via a one-pot three components condensation of isatoic anhydride, aldehydes, and ammonium salts or primary amines in the presence of aluminum methanesulfonate in EtOH/H2O solution. The catalyst is reusable and could be recycled for several runs without any distinct decrease in its efficiency. A plausible mechanism for this one-pot three components reaction was proposed. Springer Science+Business Media B.V. 2011.
- Song, Zhiguo,Liu, Lianli,Wang, Yang,Sun, Xiaohu
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experimental part
p. 1091 - 1099
(2012/09/07)
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- Strontium chloride-catalyzed one-pot synthesis of 2, 3-dihydroquinazolin- 4(1H)-ones in protic media
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A wide range of mono- and disubstituted 2, 3-dihydroquinazolin-4(1H)-ones were obtained in high yields by condensation of isatoic anhydride, aldehydes with ammonium salts or primary amines in the presence of strontium chloride in aqueous ethanol under reflux.
- Wang, Min,Zhang, Ting Ting,Liang, Yan,Gao, Jing Jing
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experimental part
p. 1423 - 1426
(2012/06/01)
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- Eco-friendly and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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A simple and facile method for the synthesis of 2,3-dihydroquinazolin-4(1H) -ones through the direct cyclocondensation of one-pot three-component cyclocondensation of isatoic anhydride, ammonium acetate (or primary amines) and aldehydes; and anthranilamide and aldehydes using silica supported ferric chloride (SiO2-FeCl3) as catalyst under solvent-free conditions is described.
- Majid, Ghashang,Kobra, Azizi,Hamed, Moulavi-Pordanjani,Hamid Reza, Shaterian
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experimental part
p. 1617 - 1623
(2012/01/05)
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- Synthesis of 2,3-dihydroquinazoline-4(1H)-ones
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An efficient, inexpensive, and heterogeneous catalyst, [Al(H 2PO4)3], was applied in a three-component, one-pot cyclocondensation reaction of isatoic anhydride with primary amines (or ammonium salts) and aldehydes to afford the corresponding quinazolinone derivatives in excellent yields. Reactions occurred under thermal solvent-free conditions. It was found that this solid acidic catalyst could be easily recovered and reused for at least three cycles without any loss of activity.
- Shaterian, Hamid Reza,Oveisi, Ali Reza,Honarmand, Moones
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scheme or table
p. 1231 - 1242
(2010/04/28)
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- A novel catalyst zinc(II) perfluorooctanoate [Zn(PFO)2]-catalyzed three-component one-pot reaction: Synthesis of quinazolinone derivatives in aqueous micellar media
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A new type of Lewis acid-surfactant-combined catalyst (LASC), zinc(II) perfluorooctanoate [Zn(PFO)2], was prepared and applied as a favorable surfactivity catalyst in three-component one-pot cyclocondensation reaction of isatoic anhydride with amines and aldehydes to afford the corresponding quinazolinone derivatives in good yields. Reactions occurred under aqueous micellar media in high atom economy. It was found that this catalyst could be easily quantitatively recovered after the reaction completed and could be reused for at least three cycles without any loss of activity. Furthermore, a mechanism to rationalize the reaction was proposed.
- Wang, Li-Min,Hu, Liang,Shao, Jue-Hua,Yu, Jianjun,Zhang, Liang
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experimental part
p. 1139 - 1145
(2009/04/07)
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- On the reaction of anthranilic acid with thionyl chloride: Iminoketene intermediate formation
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2-(Sulfinylamino) benzoyl chloride is formed on treating anthranilic acid with thionyl chloride. The formation of iminoketene intermediate from 2-(sulfinylamino) benzoyl chloride is established and the reactions carried out using the intermediate are described.
- Jacob, Dominic E.,Mathew, Lopez
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p. 664 - 668
(2008/09/18)
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- Ionic liquid promoted eco-friendly and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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2,3-Dihydroquinazolin-4(1H)-ones were efficiently synthesised by the reaction of isatoic anhydride, a primary amine or ammonium acetate, and different aromatic aldehydes in 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) without using any acidic catalyst. Also a bis-derivative of the title compound as a polyheterocyclic system was synthesised successfully in high yield.
- Dabiri, Minoo,Salehi, Peyman,Baghbanzadeh, Mostafa
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p. 1191 - 1194
(2008/03/27)
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- Water-accelerated synthesis of novel bis-2,3-dihydroquinazolin-4(1H)-one derivatives
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Bisdihydroquinazolinones were synthesized for the first time by a novel pseudo five-component condensation of isatoic anhydride, a primary amine, and a dialdehyde in water. Several solvents were examined for this reaction; however, in terms of reaction yield and time, water was found to be the optimum solvent. Georg Thieme Verlag Stuttgart.
- Baghbanzadeh, Mostafa,Salehi, Peyman,Dabiri, Minoo,Kozehgary, Gholamreza
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p. 344 - 348
(2007/10/03)
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- One-pot, three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones by montmorillonite K-10 as an efficient and reusable catalyst
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A wide range of mono- and disubstituted dihydroquinazolinones were synthesised via condensation of isatoic anhydride, primary amines, or ammonium salts with aromatic aldehydes in the presence of montmorillonite K-10. The catalyst is reusable and could be recycled for several runs without any decrease in its efficiency. Copyright Taylor & Francis Group, LLC.
- Salehi, Peyman,Dabiri, Minoo,Baghbanzadeh, Mostafa,Bahramnejad, Mahboobeh
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p. 2287 - 2292
(2007/10/03)
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- Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)- ones using KAl(SO4)2·12H2O as a reusable catalyst in water and ethanol
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KAl(SO4)2·12H2O was found to catalyze efficiently a one-pot three-component cyclocondensation of isatoic anhydride and primary amines or ammonia sources such as (NH4) 2CO3, NH4OAc and NH4Cl with aromatic aldehydes under mild conditions to afford the corresponding mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones in good yields.
- Dabiri, Minoo,Salehi, Peyman,Otokesh, Somayeh,Baghbanzadeh, Mostafa,Kozehgary, Gholamreza,Mohammadi, Ali A.
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p. 6123 - 6126
(2007/10/03)
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- A novel method for the one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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One-pot three-component condensation of isatoic anhydride with primary amines or ammonium carbonate and aromatic aldehydes in refluxing ethanol in the presence of catalytic amounts of silica sulfuric acid afforded the corresponding 2,3-dihydroquinazolin-4(1H)-ones in high yields. The catalyst is reusable and can be applied several times without any decrease in product yield.
- Salehi, Peyman,Dabiri, Minoo,Zolfigol, Mohammad Ali,Baghbanzadeh, Mostafa
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p. 1155 - 1157
(2007/10/03)
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