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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2008 - Issue 1
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Original Articles

Efficient and Inexpensive Synthesis of Benzimidazoles and Quinoxalines

B. China Raju Natural Products Laboratory, Organic Chemistry Division 1, Indian Institute of Chemical Technology, Hyderabad, IndiaCorrespondence[email protected]
,
N. Dharma Theja Natural Products Laboratory, Organic Chemistry Division 1, Indian Institute of Chemical Technology, Hyderabad, India
&
J. Ashok Kumar Natural Products Laboratory, Organic Chemistry Division 1, Indian Institute of Chemical Technology, Hyderabad, India
Pages 175-188 | Received 10 Apr 2008, Published online: 15 Feb 2011

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Cherupally Dayakar, Dondra Jyothi, Pathi Suman & Bhimapaka China Raju. (2015) Condensation of Ortho-phenylenediamines and Phenylhydrazines with Ethyl 4-Chloro-3-oxobutanoate: A Facile Approach for the Synthesis of Substituted 1H-Benzimidazoles, Pyrazolones, and Pyrazoles. Synthetic Communications 45:14, pages 1642-1651.
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Chelsea Fortenberry, Baskar Nammalwar & RichardA. Bunce. (2013) Ammonium Chloride-catalyzed Synthesis of Benzo-fused Heterocycles from o-Substituted Anilines and Orthoesters. Organic Preparations and Procedures International 45:1, pages 57-65.
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Yan-Qin Yuan & Sheng-Rong Guo. (2011) TMSCl/Fe(NO3)3-Catalyzed Synthesis of 2-Arylbenzothiazoles and 2-Arylbenzimidazoles Under Ultrasonic Irradiation. Synthetic Communications 41:14, pages 2169-2177.
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Articles from other publishers (37)

Gabriele Lupidi, Alessandro Palmieri & Marino Petrini. (2022) Sustainable and fast synthesis of functionalized quinoxalines promoted by natural deep eutectic solvents (NADESs). Green Chemistry 24:9, pages 3629-3633.
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Pranav S. Chandrachood, Amol R. Jadhav, Dinesh R. Garud, Nirmala R. Deshpande, Vedavati G. Puranik & Rajashree V. Kashalkar. (2020) An efficient method for the synthesis of quinoxaline derivatives catalyzed by titanium silicate-1. Research on Chemical Intermediates 46:12, pages 5219-5230.
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Setareh Habibzadeh, Ghasem Firouzzadeh Pasha, Mahmood Tajbakhsh, Nasim Amiri Andi & Ehsan Alaee. (2019) A novel ternary GO@SiO 2 ‐HPW nanocomposite as an efficient heterogeneous catalyst for the synthesis of benzazoles in aqueous media . Journal of the Chinese Chemical Society 66:8, pages 934-944.
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Marina Godino‐Ojer, Leticia Milla‐Diez, Inês Matos, Carlos J. Durán‐Valle, Maria Bernardo, Isabel M. Fonseca & Elena Pérez Mayoral. (2018) Enhanced Catalytic Properties of Carbon supported Zirconia and Sulfated Zirconia for the Green Synthesis of Benzodiazepines. ChemCatChem 10:22, pages 5215-5223.
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Cherupally Dayakar & BhimapakaChina Raju. (2018) A Selective Three-Component, One-Pot Approach for the Synthesis of 1,2-Dihydroquinazolines and Quinazolines. ChemistrySelect 3:32, pages 9388-9392.
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Sachin D. Pardeshi, Pratima A. Sathe, Kamlesh S. Vadagaonkar & Atul C. Chaskar. (2017) One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using N -Bromosuccinimide . Advanced Synthesis & Catalysis 359:23, pages 4217-4226.
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V. D. Gvozdev, K. N. Shavrin, E. G. Baskir, M. P. Egorov & O. M. Nefedov. (2017) Cyclization of alk-4-ynals with o-diaminoarenes as a selective one-pot synthesis of arylmethylidene-substituted 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles and 7,8-dihydro-6H-pyrrolo[1’,2’:1,2]imidazo[4,5-b]pyridines. Russian Chemical Bulletin 65:7, pages 1829-1838.
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Valentin D. Gvozdev, Konstantin N. Shavrin, Mikhail P. Egorov & Oleg M. Nefedov. (2016) Stereoselective one-pot synthesis of (1Z)- and (1E)-1-arylmethylidene-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles by cyclization of alk-4-ynals with o-diaminobenzene. Mendeleev Communications 26:1, pages 3-5.
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Vakhid A. MamedovVakhid A. Mamedov. 2016. Quinoxalines. Quinoxalines 5 133 .
Valentin D. Gvozdev, Konstantin N. Shavrin, Mikhail P. Egorov & Oleg M. Nefedov. (2015) One-pot synthesis of 1-arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a]-[3,1]benzoxazines and 1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]-quinazolines from 5-arylalk-4-ynals and o-aminobenzylic alcohol/amine. Mendeleev Communications 25:5, pages 329-331.
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Vijayakumar Badathala. (2015) Acid treated clays: preparation, characterization and catalytic activity for synthesis of quinoxaline derivatives. Journal of Porous Materials 22:3, pages 779-786.
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Kamlesh S. Vadagaonkar, Hanuman P. Kalmode, Kaliyappan Murugan & Atul C. Chaskar. (2015) I 2 catalyzed tandem protocol for synthesis of quinoxalines via sp 3 , sp 2 and sp C–H functionalization . RSC Advances 5:8, pages 5580-5590.
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Goutam Brahmachari. 2015. Room Temperature Organic Synthesis. Room Temperature Organic Synthesis 75 188 .
Mingcong Qin, Yujie Fu, Xiqing Wang, Yuhang Zhang & Weidong Ma. (2014) Green synthesis of benzimidazole derivatives catalyzed by ionic liquid under microwave irradiation. Journal of the Iranian Chemical Society 11:6, pages 1553-1559.
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Farahnaz K. Behbahani, Elham Rezaee & Zahra Fakhroueian. (2014) Synthesis of 2-Substituted Benzimidazoles Using 25 % Co/Ce-ZrO2 as a Heterogeneous and Nanocatalyst. Catalysis Letters 144:12, pages 2184-2190.
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Dnyaneshwar B. Gophane, Burkhard Endeward, Thomas F. Prisner & Snorri Th. Sigurdsson. (2014) Conformationally Restricted Isoindoline-Derived Spin Labels in Duplex DNA: Distances and Rotational Flexibility by Pulsed Electron-Electron Double Resonance Spectroscopy. Chemistry - A European Journal 20:48, pages 15913-15919.
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Manjaree A. Satam, Rahul D. Telore & Nagaiyan Sekar. (2014) Photophysical properties of Schiff’s bases from 3-(1,3-benzothiazol-2-yl)-2-hydroxy naphthalene-1-carbaldehyde. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 132, pages 678-686.
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Lijiu Gao, Rui Liu, Chenxia Yu, Changsheng Yao, Tuanjie Li & Zhaoxin Xiao. (2013) NHC-initiated cascade, metal-free synthesis of quinoxaline derivatives under solvent-free conditions. Research on Chemical Intermediates 40:5, pages 2131-2138.
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Priyabrata Das & Jef K. De Brabander. (2013) RETRACTED: A room temperature copper catalyzed N-selective arylation of β-amino alcohols with iodoanilines and aryl iodides. Tetrahedron 69:36, pages 7646-7652.
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Luba Ignatovich, Olga Starkova, Vitalijs Romanovs, Ilze Sleiksha, Irina Shestakova, Jury Popelis & Edmunds Lukevics. (2013) Novel trialkylsilyl(germyl)-substituted thienyl- and furylbenzimidazoles and their N-substituted derivatives – synthesis, structure and cytotoxic activity. Comptes Rendus Chimie 16:6, pages 621-627.
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Guo-Feng Chen, Hai-Dong Shen, Hui-Ming Jia, Li-Yan Zhang, Hong-Yan Kang, Qing-Qing Qi, Bao-Hua Chen, Jia-Li Cao & Ji-Tai Li. (2013) Eco-Friendly Synthesis of 2-Substituted Benzimidazoles Using Air as the Oxidant. Australian Journal of Chemistry 66:2, pages 262.
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Amit K. Chaturvedi, Arvind S. Negi & Puja Khare. (2013) A simple and straightforward synthesis of substituted 2-arylbenzimidazoles over silica gel. RSC Advances 3:14, pages 4500.
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OMPRAKASH B PAWAR, FULCHAND R CHAVAN, VENKAT S SURYAWANSHI, VISHNU S SHINDE & NARAYAN D SHINDE. (2013) Thiamine hydrochloride: An efficient catalyst for one-pot synthesis of quinoxaline derivatives at ambient temperature. Journal of Chemical Sciences 125:1, pages 159-163.
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Farahnaz K. Behbahani & Parisa Ziaei. (2012) One-pot synthesis of 2-substituted benzimidazoles catalyzed by anhydrous FePO4. Chemistry of Heterocyclic Compounds 48:7, pages 1011-1017.
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Keith S. Learn, Jason C. Wagner, Mark S. Albom, Thelma S. Angeles, Zeqi Huang, Arup K. Ghose, Weihua Wan, Mangeng Cheng, Bruce D. Dorsey & Gregory R. Ott. (2012) Design of 7-amino-6-chloro-3H-imidazo[4,5-b]pyridine scaffold from 5-chloro-2,4-diaminopyrimidine pharmacophore: identification of potent inhibitors of anaplastic lymphoma kinase. MedChemComm 3:9, pages 1138.
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Vakhid A. Mamedov & Nataliya A. Zhukova. 2012. 55 88 .
Susmita Paul & Basudeb Basu. (2011) Synthesis of libraries of quinoxalines through eco-friendly tandem oxidation–condensation or condensation reactions. Tetrahedron Letters 52:49, pages 6597-6602.
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Farahnaz K. Behbahani, Parisa Ziaei, Zahra Fakhroueian & Neda Doragi. (2011) An efficient synthesis of 2-arylbenzimidazoles from o-phenylenediamines and arylaldehydes catalyzed by Fe/CeO2–ZrO2 nano fine particles. Monatshefte für Chemie - Chemical Monthly 142:9, pages 901-906.
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Jarugu Narasimha Moorthy & Ishita Neogi. (2011) IBX-mediated one-pot synthesis of benzimidazoles from primary alcohols and arylmethyl bromides. Tetrahedron Letters 52:30, pages 3868-3871.
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Heiko Leutbecher, Mihaela-Anca Constantin, Sabine Mika, Jürgen Conrad & Uwe Beifuss. (2011) A new laccase-catalyzed domino process and its application to the efficient synthesis of 2-aryl-1H-benzimidazoles. Tetrahedron Letters 52:5, pages 605-608.
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Magdy Ahmed Ibrahim. (2011) Synthetic Utilities of o-Phenylenediamines: Synthetic Approaches for Benzimidazoles, Quinoxalines and Benzo[1,5]diazepines. HETEROCYCLES 83:12, pages 2689.
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K. Padmavathy, Gopalpur Nagendrappa & K.V. Geetha. (2011) A rapid synthesis of quinoxalines starting from ketones. Tetrahedron Letters 52:4, pages 544-547.
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Larry Yet. 2011. 217 257 .
Valentine G. Nenajdenko, Vasiliy M. Muzalevskiy, Aleksey V. Shastin, Elizabeth S. Balenkova, Evgeniy V. Kondrashov, Igor A. Ushakov & Alexander Yu. Rulev. (2010) Fragmentation of Trifluoromethylated Alkenes and Acetylenes by N , N -Binucleophiles. Synthesis of Imidazolines or Imidazolidines (Oxazolidines) Controlled by Substituent . The Journal of Organic Chemistry 75:16, pages 5679-5688.
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B. China Raju, Ashok K. Tiwari, J. Ashok Kumar, A. Zehra Ali, Sachin B. Agawane, G. Saidachary & K. Madhusudana. (2010) α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives. Bioorganic & Medicinal Chemistry 18:1, pages 358-365.
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GK Surya PrakashHabiba VaghooArthi VenkatChiradeep PanjaSujith ChackoThomas MathewGeorge A Olah. (2009) Gallium (III) triflate-catalyzed synthesis of heterocycles: quinoxalines, 1,5-benzodiazepines and their fluorinated derivatives. Future Medicinal Chemistry 1:5, pages 909-920.
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B. Cina Raju, N. Dharma Theja & J. Ashok Kumar. (2009) ChemInform Abstract: Efficient and Inexpensive Synthesis of Benzimidazoles and Quinoxalines.. ChemInform 40:25.
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