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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 3
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Original Articles

An Efficient Method for the Oxidation of Hantzsch 1,4-Dihydropyridines to their Corresponding Pyridine Derivatives Under Mild and Heterogeneous Conditions

Mohammad Ali Zolfigol Chemistry Department, College of Science, Bu-Ali Sina University, Hamadan, 65174, I.R., Iran
,
Maryam Kiany-Borazjani Chemistry Department, College of Science, Bu-Ali Sina University, Hamadan, 65174, I.R., Iran
,
Majid M. Sadeghi Chemistry Department, College of Science, Isfahan University, Isfahan, I.R., Iran
,
Iraj Mohammadpoor-Baltork Chemistry Department, College of Science, Isfahan University, Isfahan, I.R., Iran
&
Hamid Reza Memarian Chemistry Department, College of Science, Isfahan University, Isfahan, I.R., Iran
Pages 551-558 | Received 13 Apr 1999, Published online: 04 Dec 2007

Citations (44)

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Masoud Nasr-Esfahani, Majid Moghadam & Ghasem Valipour. (2009) Efficient Oxidation of Hantzsch 1,4-Dihydropyridines with Tetrabutylammonium Peroxomonosulfate Catalyzed by Manganese(III) Schiff Base Complexes: The Effect of Schiff Base Complex on the Product Selectivity. Synthetic Communications 39:21, pages 3867-3879.
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Lotfi Shiri & Arash Ghorbani-Choghamarani. (2009) Chemoselective Oxidation of Benzylic Alcohols and Hydroquinones with bis-(2,4,6-Trimethylpyridinium) Dichromate (BTMPDC) as an Efficient and New Oxidizing Agent. Phosphorus, Sulfur, and Silicon and the Related Elements 184:2, pages 492-498.
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Mohammad Ali Zolfigol, Peyman Salehi, Arash Ghorbani-Choghamarani, Maliheh Safaiee & Mozhgan Shahamirian. (2007) Silica Chromate as a Novel Oxidizing Agent for the Oxidation of 1,4‐Dihydropyridines. Synthetic Communications 37:11, pages 1817-1823.
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Behzad Zeynizadeh, Karim Akbari Dilmaghani & Asli Roozijoy. (2005) Oxidative‐Aromatization of Hantzsch Ester 1,4‐Dihydropyridines by KBrO3/SnCl4 · 5H2O Under Mild Condition. Synthetic Communications 35:4, pages 557-562.
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Mohammad Ali Zolfigol, Farhad Shirini, Arash Ghorbani Choghamarani & Iraj Mohammadpoor-Baltork. (2003) Silica Chloride/NaNO 2 as a Novel Heterogeneous System for the Oxidation of 1,4-Dihydropyridines Under Mild Conditions via In Situ Generation of NOCl. Phosphorus, Sulfur, and Silicon and the Related Elements 178:8, pages 1709-1715.
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Mohammad Ali Zolfigol, Gholamabbas Chehardoli & Shadpour E. Mallakpour. (2003) Silica Sulfuric Acid/NaNO2 as a Novel Heterogeneous System for the Oxidation of Urazoles Under Mild Conditions. Synthetic Communications 33:5, pages 833-841.
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Mohammad Ali Zolfigol, Mohammad Hassan Zebarjadian, Iraj Mohammadpoor-Baltork & Mojtaba Shamsipur. (2002) DEPROTECTION OF 1,1-DIACETATES WITH [NO+ ⋅ CROWN ⋅ H(NO3)2 −]. Synthetic Communications 32:18, pages 2803-2808.
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Jafar Asgarian Damavandi, Mohammad Ali Zolfigol & Bahador Karami. (2001) OXIDATION OF 1,2-DIHYDROQUINOLINES UNDER MILD AND HETEROGENEOUS CONDITIONS. Synthetic Communications 31:20, pages 3183-3187.
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Mohammad Ali Zolfigol, Mojtaba Bagherzadeh, Arash Ghorbani Choghamarani, Hassan Keypour & Sadegh Salehzadeh. (2001) N-NITROSATION OF SECONDARY AMINES UNDER MILD AND HETEROGENEOUS CONDITIONS. Synthetic Communications 31:8, pages 1161-1166.
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Mohammad Ali Zolfigol, Mojtaba Bagherzadeh, Gholamabbas Chehardoli & Shadpour E. Mallakpour. (2001) OXIDATION OF URAZOLES UNDER MILD AND HETEROGENEOUS CONDITIONS WITH KHSO5 AND NaNO2 . Synthetic Communications 31:8, pages 1149-1154.
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Mohammad Ali Zolfigol, Mohammad Hassan Zebarjadian, Majid M. Sadegh, Iraj Mohammadpoor-Baltork, Hamid Reza Memarian & Mojtaba Shamsipur. (2001) CHEMOSELECTIVE OXIDATION OF 1,4-DIHYDROPYRIDINES WITH [NO+.CROWN.H(NO3)2 −]. Synthetic Communications 31:6, pages 929-934.
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Mohammad Ali Zolfigol, Arash Ghorbani Choghamarani, Farhad Shirini, Hassan Keypour & Sadegh Salehzadeh. (2001) CHEMOSELECTIVE N-NITROSATION OF SECONDARY AMINES UNDER MILD AND HETEROGENEOUS CONDITIONS. Synthetic Communications 31:3, pages 359-365.
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Articles from other publishers (32)

Subbiah SowmiahJosé M. S. S. Esperança, Luís P. N. Rebelo & Carlos A. M. Afonso. (2018) Pyridinium salts: from synthesis to reactivity and applications. Organic Chemistry Frontiers 5:3, pages 453-493.
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Mannar R. Maurya, Bithika Sarkar, Fernando Avecilla & Isabel Correia. (2016) Vanadium( iv and v ) complexes of pyrazolone based ligands: Synthesis, structural characterization and catalytic applications . Dalton Transactions 45:43, pages 17343-17364.
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Lais D. Guanaes, Diogo R.B. Ducatti, M. Eugênia R. Duarte, Sandra M.W. Barreira, Miguel D. Noseda & Alan G. Gonçalves. (2015) Synthesis of pyridinium salts from N-substituted dihydropyridines with BF3OEt2 in the absence of added oxidants. Tetrahedron Letters 56:15, pages 2001-2004.
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Ivan N. Bardasov, Anastasiya U. Alekseeva, Denis L. Mihailov, Oleg V. Ershov, Oleg E. Nasakin & Viktor A. Tafeenko. (2014) One-pot synthesis of 2-(dicyanomethylene)-1,2-dihydropyridine derivatives. Tetrahedron Letters 55:16, pages 2730-2733.
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Mladen Litvić, Maja Regović, Karolina Šmic, Marija Lovrić & Mirela Filipan-Litvić. (2012) Remarkably fast and selective aromatization of Hantzsch esters with MoOCl4 and MoCl5: A chemical model for possible biologically relevant properties of molybdenum-containing enzymes. Bioorganic & Medicinal Chemistry Letters 22:11, pages 3676-3681.
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Ajam C. Shaikh & Chinpiao Chen. (2010) Facile and efficient aromatization of 1,4-dihydropyridines with M(NO3)2·XH2O, TNCB, TBAP and HMTAI and preparation of deuterium labeled dehydronifedipine from nifedipine-d3. Bioorganic & Medicinal Chemistry Letters 20:12, pages 3664-3668.
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Mirela Filipan-Litvić, Mladen Litvić & Vladimir Vinković. (2008) Rapid, efficient, room temperature aromatization of Hantzsch-1,4-dihydropyridines with vanadium(V) salts: superiority of classical technique versus microwave promoted reaction. Tetrahedron 64:48, pages 10912-10918.
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Mirela Filipan-Litvić, Mladen Litvić & Vladimir Vinković. (2008) A highly efficient biomimetic aromatization of Hantzsch-1,4-dihydropyridines with t-butylhydroperoxide, catalysed by iron(III) phthalocyanine chloride. Bioorganic & Medicinal Chemistry 16:20, pages 9276-9282.
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Mirela Filipan-Litvić, Mladen Litvić & Vladimir Vinković. (2008) An efficient, metal-free, room temperature aromatization of Hantzsch-1,4-dihydropyridines with urea–hydrogen peroxide adduct, catalyzed by molecular iodine. Tetrahedron 64:24, pages 5649-5656.
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Galla Srihari, Manda Nagaraju & Madugula Marthanda Murthy. (2007) Solvent‐Free One‐Pot Synthesis of Amidoalkyl Naphthols Catalyzed by Silica Sulfuric Acid. Helvetica Chimica Acta 90:8, pages 1497-1504.
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Vajiravelu Sivamurugan, Velayutham Murugesan, Valiyaveettil Suresh, Muthaiyahpillai Palanichamy & Ajayan Vinu. (2009) BIFC and QFC promoted rapid and cleaner aromatization of 1,4‐dihydropyridines under solvent‐free condition. Journal of Heterocyclic Chemistry 44:4, pages 973-977.
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Hadi Adibi & Abdol Reza Hajipour. (2007) A convenient and efficient protocol for oxidative aromatization of Hantzsch 1,4-dihydropyridines using benzyltriphenylphosphonium peroxymonosulfate under almost neutral reaction conditions. Bioorganic & Medicinal Chemistry Letters 17:4, pages 1008-1012.
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Majid Moghadam, Masoud Nasr-Esfahani, Shahram Tangestaninejad & Valiollah Mirkhani. (2006) Mild and efficient oxidation of Hantzsch 1,4-dihydropyridines with sodium periodate catalyzed by a new polystyrene-bound Mn(TPP)Cl. Bioorganic & Medicinal Chemistry Letters 16:7, pages 2026-2030.
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Hamid R. Memarian, Iraj Mohammadpoor-Baltork & Mohsen Javahery. (2006) Aromatization of Various 1,4-Dihydropyridines by Tetrabutylphosphonium Dichromate (TBPDC) under Conventional Heating and Microwave Irradiation. Journal of the Chinese Chemical Society 53:2, pages 511-514.
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Majid M. Heravi, Fatemeh Derikvand, Hossein A. Oskooie & Rahim Hekmatshoar. (2019) Zeofen: A User Friendly Agent for Oxidation of the Hantzsch 1, 4-Dihydropyridines. Journal of Chemical Research 2006:3, pages 168-169.
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Khodabakhsh Niknam, Seyed Mehdi Razavian, Mohammah Ali Zolfigol & Iraj Mohammahpoor‐Baltork. (2009) Aromatization of 1,4‐dihydropyridines in the presence of methanesulfonic acid/NaNO 2 /wet SiO 2 under both heterogeneous and solvent free conditions . Journal of Heterocyclic Chemistry 43:1, pages 199-202.
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Behzad Zeynizadeh, Karim Akbari Dilmaghani & Asli Roozijoy. (2019) KBrO 3 /FeCl 3 as an Efficient Oxidising System for Aromatisation of Hantzsch 1,4-dihydropyridines in Wet Acetonitrile . Journal of Chemical Research 2005:10, pages 657-658.
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Behzad Zeynizadeh, Karim Akbari Dilmaghani & Asli Roozijoy. (2005) Aromatization of Hantzsch Ester 1,4-Dihydropyridines with Iodine under Normal Conditions and Ultrasound Irradiation. Journal of the Chinese Chemical Society 52:5, pages 1001-1004.
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Mohammad Ali Zolfigol, Arash Ghorbani Choghamarani, Mozhgan Shahamirian, Maliheh Safaiee, Iraj Mohammadpoor-Baltork, Shadpour Mallakpour & Mohammad Abdollahi-Alibeik. (2005) 4-Phenyl-1,2,4-triazole-3,5-dione as a novel and reusable reagent for the aromatization of 1,4-dihydropyridines under mild conditions. Tetrahedron Letters 46:33, pages 5581-5584.
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Mladen Litvić, Ivica Cepanec, Mirela Filipan, Karmen Kos, Anamarija Bartolinčić, Vinka Drušković, Mohamed Majed Tibi & Vladimir Vinković. (2005) Mild, Selective and High-Yield Oxidation of Hantzsch 1,4-Dihydropyridines with Lead(IV) Acetate. HETEROCYCLES 65:1, pages 23.
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Michael B. Smith. 2003. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 115 225 .
. (2003) Chemoselective N-Nitrosation of Secondary Amines under Mild and Heterogeneous Conditions. Bulletin of the Korean Chemical Society 24:5, pages 638-640.
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Mohammad Ali ZolfigolArash Ghorbani ChoghamaraniSolmaz DialamehMajid M. Sadeghi, Iraj Mohammadpoor-Baltork & Hamid Reza Memarian. (2019) An Efficient Method for the Oxidation of 1,4-Dihydropyridines under Mild and Heterogeneous Conditions via in Situ Generation of NOCl . Journal of Chemical Research 2003:1, pages 18-20.
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Mohammad Ali Zolfigol. (2001) Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions. Tetrahedron 57:46, pages 9509-9511.
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Mohammad Ali Zolfigol, Mojtaba Bagherzadeh, Gholamabbass Chehardoli, Shadpour E Mallakpour & Manochehr Mamaghani. (2019) Oxidation of urazoles via in situ generation of Cl + by using N,N,2,3,4,5,6-heptachloroaniline or a UHP/MCl n system under mild conditions . Journal of Chemical Research 2001:9, pages 390-393.
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Mohammad Ali Zolfigol, Mehdi Torabi & Shadpour E Mallakpour. (2001) Silica chloride/NaNO2 as a novel heterogeneous system for the oxidation of urazoles under mild conditions. Tetrahedron 57:39, pages 8381-8384.
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Mohammad Zolfigol. (2001) An Efficient and Chemoselective Method for Oximination of β-Diketones Under Mild and Heterogeneous Conditions. Molecules 6:8, pages 694-698.
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Mohammad Ali ZolfigolMohammad Hassan ZebarjadianGholamabbas ChehardoliHassan KeypourSadegh SalehzadehMojtaba Shamsipur. (2001) N-Nitrosation of Secondary Amines with [NO + ·Crown·H(NO 3 ) 2 - ] . The Journal of Organic Chemistry 66:10, pages 3619-3620.
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Mohammad Ali Zolfigol, Mojtaba Bagherzadeh, Elahe Madrakian, Ezat Ghaemi & Abolfazl Taqian-Nasab. (2019) One-pot Nitration of Phenols under Mild and Heterogeneous Conditions. Journal of Chemical Research 2001:4, pages 140-142.
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Mohammad Ali Zolfigol, Mohammad Hassan Zebarjadian, Gholamabbas Chehardoli, Shadpour E Mallakpour & Mojtaba Shamsipur. (2001) An efficient method for the oxidation of urazoles with [NO+·crown·H(NO3)2−]. Tetrahedron 57:8, pages 1627-1629.
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Mohammad Ali Zolfigol, Farhad Shirini, Arash Ghorbani Choghamarani, Abolfazl Taqian-Nasab, Hassan Keypour & Sadegh Salehzadeh. (2019) Chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions via in situ generation of NOCl. Journal of Chemical Research 2000:9, pages 420-422.
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Mohammad Ali Zolfigol, Maryam Kiany‐Borazjani, Majid M. Sadeghi, Iraj Mohammadpoor‐Baltork & Hamid Reza Memarian. (2010) ChemInform Abstract: An Efficient Method for the Oxidation of Hantzsch 1,4‐Dihydropyridines to Their Corresponding Pyridine Derivatives under Mild and Heterogeneous Conditions.. ChemInform 31:24.
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