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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 16
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Original Articles

Dehydrogenation of Imidazolines to Imidazoles with Pd-Carbon

Yoshiya Amemiya Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, Ohio, 43210
,
Duane D. Miller Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, 500 West 12th Avenue, Columbus, Ohio, 43210
&
Fu-Lian Hsu U.S. Army Chemical Research, Development and Engineering Center, Aberdeen Proving Ground, Maryland, 21010-5423
Pages 2483-2489 | Received 15 Jun 1990, Published online: 24 Oct 2006

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Hadi Kargar, Saeideh Afkhami & Fatemeh Alikhani. (2012) Green oxidation of 2-imidazolines with tert-butyl hydroperoxide catalyzed by supported manganese(III) porphyrin in water. Journal of Coordination Chemistry 65:19, pages 3502-3510.
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Articles from other publishers (30)

Thaipparambil Aneeja, Sankaran Radhika, Mohan Neetha & Gopinathan Anilkumar. (2020) An Overview of the One-pot Synthesis of Imidazolines. Current Organic Chemistry 24:20, pages 2341-2355.
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Maxime Beuvin, Maxime Manneveau, Sonia Diab, Baptiste Picard, Morgane Sanselme, Serge R. Piettre, Julien Legros & Isabelle Chataigner. (2018) New synthesis of imidazole derivatives from cyanobenzenes. Tetrahedron Letters 59:51, pages 4487-4491.
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Anggi Eka Putra, Yohei Oe & Tetsuo Ohta. (2015) Pd/C‐Catalyzed Alkylation of Heterocyclic Nucleophiles with Alcohols through the “Borrowing Hydrogen” Process. European Journal of Organic Chemistry 2015:35, pages 7799-7805.
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Pakornwit Sarnpitak, Prashant Mujumdar, Christophe Morisseau, Sung Hee Hwang, Bruce Hammock, Vladimir Iurchenko, Sergey Zozulya, Antonis Gavalas, Athina Geronikaki, Yan Ivanenkov & Mikhail Krasavin. (2014) Potent, orally available, selective COX-2 inhibitors based on 2-imidazoline core. European Journal of Medicinal Chemistry 84, pages 160-172.
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Shota Aiki, Yuhei Kijima, Junpei Kuwabara, Ayako Taketoshi, Take-aki Koizumi, Shigehisa Akine & Takaki Kanbara. (2013) Ligand Modification of Cyclometalated Ruthenium Complexes in the Aerobic Oxidative Dehydrogenation of Imidazolines. ACS Catalysis 3:5, pages 812-816.
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Pakornwit Sarnpitak & Mikhail Krasavin. (2013) Synthesis of 1,2,4-triazoles employing isocyanides. Tetrahedron 69:10, pages 2289-2295.
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Yue Huang, Xiaodong Zu, Fan Wu, Jinyi Xu, Xiaoming Wu & Hequan Yao. (2012) Highly efficient oxidation of 2-imidazoline-5-carboxylic derivatives to imidazole-5-carboxylic derivatives by dioxygen. Tetrahedron 68:14, pages 3123-3128.
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Hadi Kargar. (2011) Rapid and efficient biomimetic oxidation of 2-imidazolines to their corresponding imidazoles with NaIO4 catalyzed by Mn(salophen)Cl. Inorganic Chemistry Communications 14:6, pages 863-866.
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Hadi Kargar, Majid Moghadam, Valiollah Mirkhani, Shahram Tangestaninejad, Iraj Mohammadpoor-Baltork & Mahmood Naghipour. (2011) Oxidation of 2-imidazolines to 2-imidazoles with sodium periodate catalyzed by polystyrene-bound manganese(III) porphyrin. Polyhedron 30:9, pages 1463-1468.
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Hadi Kargar, Majid Moghadam, Valiollah Mirkhani, Shahram Tangestaninejad, Iraj Mohammadpoor-Baltork & Iman Nameni. (2011) Dehydrogenation of 2-imidazolines with sodium periodate catalyzed by manganese(III) tetraphenylporphyrin. Bioorganic & Medicinal Chemistry Letters 21:7, pages 2146-2148.
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Jianjun Chen, Zhao Wang, Chien-Ming Li, Yan Lu, Pavan K. Vaddady, Bernd Meibohm, James T. Dalton, Duane D. Miller & Wei Li. (2010) Discovery of Novel 2-Aryl-4-benzoyl-imidazoles Targeting the Colchicines Binding Site in Tubulin As Potential Anticancer Agents. Journal of Medicinal Chemistry 53:20, pages 7414-7427.
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H. Adibi, A. R. Hajipour & H. Jafari. (2008) Metal-free oxidative dehydrogenation of imidazolines and pyrazolines using silica-adsorbed peroxymonosulfate under aprotic and almost neutral conditions. Chemistry of Heterocyclic Compounds 44:7, pages 802-806.
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Yurngdong Jahng & A. F. M. Motiur Rahman. (2008) Benzo[b]-1,10-phenanthrolines. V. Synthesis and Properties of 3,3’-Polymethylene-2-(pyrid-2’-yl)benzo[b]-1,10-phenanthrolines. HETEROCYCLES 75:10, pages 2507.
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N. Xi, Q. Huang & L. Liu. 2008. Comprehensive Heterocyclic Chemistry III. Comprehensive Heterocyclic Chemistry III 143 364 .
Y. B. R. D. Rajesh, Subramania Ranganathan, Richard D. Gilardi & Isabella L. Karle. (2007) Differing Patterns in the Self-Assembly of Radially Anchored Imidazoles, 1,3,5-Tris(1H-imidazol-2-yl)benzene and 1,3-Bis(1H-imidazol-2-yl)benzene. Journal of Chemical Crystallography 38:1, pages 39-48.
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Satoshi Haneda, Ayaka Okui, Chigusa Ueba & Masahiko Hayashi. (2007) An efficient synthesis of 2-arylimidazoles by oxidation of 2-arylimidazolines using activated carbon–O2 system and its application to palladium-catalyzed Mizoroki–Heck reaction. Tetrahedron 63:11, pages 2414-2417.
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Midori Ishihara & Hideo Togo. (2007) Direct oxidative conversion of aldehydes and alcohols to 2-imidazolines and 2-oxazolines using molecular iodine. Tetrahedron 63:6, pages 1474-1480.
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Yurngdong Jahng & A. F. M. Motiur Rahman. (2007) Synthesis and Properties of 3,2’-Polymethylene-2-phenylbenzo[b]-1,10-phenanthrolines. HETEROCYCLES 71:9, pages 2003.
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Hiromichi Fujioka, Kenichi Murai, Ozora Kubo, Yusuke Ohba & Yasuyuki Kita. (2007) One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates. Tetrahedron 63:3, pages 638-643.
Crossref
Patrik Pařík, Sylva Šenauerová, Vlasta Lišková, Karel Handlíř & Miroslav Ludwig. (2009) Study of synthesis of 2‐(2‐alkoxyphenyl)‐1 H ‐imidazoles. Comparison of oxidative aromatization reactions of imidazolines . Journal of Heterocyclic Chemistry 43:4, pages 835-841.
Crossref
Iraj Mohammadpoor-Baltork & Mohammad Abdollahi-Alibeik. (2005) Mild, efficient, and chemoselective dehydrogenation of 2-imidazolines, bis-imidazolines, and N -substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10 . Canadian Journal of Chemistry 83:2, pages 110-114.
Crossref
Mohammad Abdollahi-Alibeik, Iraj Mohammadpoor-Baltork & Mohammad Ali Zolfigol. (2004) Alumina supported potassium permanganate: an efficient reagent for chemoselective dehydrogenation of 2-imidazolines under mild conditions. Bioorganic & Medicinal Chemistry Letters 14:24, pages 6079-6082.
Crossref
Iraj Mohammadpoor-Baltork, Mohammad Ali Zolfigol & Mohammad Abdollahi-Alibeik. (2004) Novel and chemoselective dehydrogenation of 2-substituted imidazolines with potassium permanganate supported on silica gel. Tetrahedron Letters 45:47, pages 8687-8690.
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K. C. Nicolaou, Casey J. N. Mathison & Tamsyn Montagnon. (2004) o -Iodoxybenzoic Acid (IBX) as a Viable Reagent in the Manipulation of Nitrogen- and Sulfur-Containing Substrates:  Scope, Generality, and Mechanism of IBX-Mediated Amine Oxidations and Dithiane Deprotections . Journal of the American Chemical Society 126:16, pages 5192-5201.
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Nicola A. Boland, Mike Casey, Stephen J. Hynes, Jonathan W. Matthews, Helge Müller-Bunz & Philippa Wilkes. (2004) Preparation of enantiopure biimidazoline ligands and their use in asymmetric catalysis. Org. Biomol. Chem. 2:14, pages 1995-2002.
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Michael J Bishop, Kevin A Barvian, Judd Berman, Eric C Bigham, Deanna T Garrison, Michael J Gobel, Stephen J Hodson, Paul E Irving, James A Liacos, Frank Navas, III, David L SaussyJr.Jr. & Jason D Speake. (2002) α1-Adrenoceptor Agonists: The Identification of Novel α1A Subtype Selective 2′-Heteroaryl-2-(phenoxymethyl)imidazolines. Bioorganic & Medicinal Chemistry Letters 12:3, pages 471-475.
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Mohammad. A. Bigdeli, Mir.M.Alavi Nikje, Said Jafari & Majid M. Heravi. (2019) Regioselective Synthesis of syn -oximes using 3Å Molecular Sieves in a Solventless System . Journal of Chemical Research 2002:1, pages 20-21.
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M.Ross Grimmett. 1997. Imidazole and Benzimidazole Synthesis. Imidazole and Benzimidazole Synthesis 167 191 .
Yong Hae Kim & Jun Young Choi. (1996) Novel palladium catalyzed dehydrogenation of ?-hydrazinonitriles to hydrazonoyl cyanides using cyclopentene. Synthesis of 1H-pyrazole-4-carboxylate. Tetrahedron Letters 37:48, pages 8771-8774.
Crossref
Y. AMEMIYA, D. D. MILLER & F.‐L. HSU. (2010) ChemInform Abstract: Dehydrogenation of Imidazolines to Imidazoles with Pd‐Carbon.. ChemInform 22:12.
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