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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 3-4
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Original Articles

Synthesis of Amines by Reduction of Imines with the MCl2/NaBH4 (M = Co, Ni) System

M. Periasamy School of Chemistry, University of Hyderabad Central University, P.O., Hyderabad, 500 134, India
,
A. Devasagayaraj School of Chemistry, University of Hyderabad Central University, P.O., Hyderabad, 500 134, India
,
N. Satyanarayana School of Chemistry, University of Hyderabad Central University, P.O., Hyderabad, 500 134, India
&
C. Narayana School of Chemistry, University of Hyderabad Central University, P.O., Hyderabad, 500 134, India
Pages 565-573 | Received 09 Aug 1988, Published online: 23 Oct 2006

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Shripad Patil, Ashwini Bedre, Vilas Gade, Manohar Jopale, Ravindra Bhagat & Ashok Pise. (2023) One-pot protocol for the reductive amination of aldehydes using thiamine hydrochloride as a green catalyst under solvent-free condition. Synthetic Communications 53:18, pages 1545-1558.
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V. Sridharan, S. Muthusubramanian & S. Sivasubramanian. (2004) A Facile Reduction Procedure for N,N′‐bis[5‐Substituted Salicylidene]‐m/p‐phenylenediamines with Sodium Borohydride–Silica Gel System. Synthetic Communications 34:6, pages 1087-1096.
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S. Chandrasekhar, M. Venkat Reddy & L. Chandraiah. (1999) Inexpensive Protocol for Reduction of Imines to Amines Using Polymethylhydrosiloxane (PMHS). Synthetic Communications 29:22, pages 3981-3987.
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Li Sheng Jian, Mi Aiqiao, Yang Guishu & Jiang Yaozhong. (1992) Facile Preparation of Some Highly Hindered Chiral 1,2-Diphenyl-2-(N-monoalkyl)amino Alcohols and N-Benzylbornamine. Synthetic Communications 22:10, pages 1497-1503.
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Articles from other publishers (34)

I. Yu. Chukicheva, O. A. Shumova, O. G. Shevchenko & A. V. Kutchin. (2024) Synthesis of N- and C-terpenylanilines and the study of their properties. Russian Chemical Bulletin 73:3, pages 580-587.
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Shripad M Patil, Ashwini V Bedre, Vilas B Gade & Manohar K Jopale. (2023) Metal-free, an effective and one-pot protocol for the reductive amination of aldehydes using glycerol as a green solvent. Journal of Chemical Sciences 135:2.
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R. V. Brunilin, A. A. Vernigora, O. V. Vostrikova, A. V. Davidenko, M. B. Nawrozkij, N. A. Salykin & I. A. Novakov. (2022) Development and competitive evaluation of methods for the reduction of (het)arylimines of cage-structured monoterpenoid ketones. Russian Chemical Bulletin 71:8, pages 1662-1669.
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Prerna Ganwir & Ganesh Chaturbhuj. (2021) Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4. Tetrahedron Letters 74, pages 153143.
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Oleg I. Afanasyev, Artemy R. Fatkulin, Pavel N. Solyev, Ivan Smirnov, Artem Amangeldyev, Sergey E. Semenov & Denis Chusov. (2020) Direct Reductive Amination of Camphor Using Iron Pentacarbonyl as Stoichiometric Reducing Agent: Features and Limitations. European Journal of Organic Chemistry 2020:39, pages 6289-6294.
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Steven W. Goldstein & Amely V. Cross. (2015) Solvent-Free Reductive Amination: An Organic Chemistry Experiment. Journal of Chemical Education 92:7, pages 1214-1216.
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ATULYA NAGARSENKAR, SANTOSH KUMAR PRAJAPTI & BATHINI NAGENDRA BABU. (2015) An efficient catalytic reductive amination: A facile one-pot access to 1,2-dihydropyrrolo[3,4-b]indol-3(4H)-ones by using B(C 6 F 5 ) 3 /NaBH 4. Journal of Chemical Sciences 127:4, pages 711-716.
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Carolin Edinger, Jörn Kulisch & Siegfried R Waldvogel. (2015) Stereoselective cathodic synthesis of 8-substituted (1 R ,3 R ,4 S )-menthylamines . Beilstein Journal of Organic Chemistry 11, pages 294-301.
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Hakimeh Ziyadi & Akbar Heydari. (2014) Core–Shell α-Fe2O3@SiO2 Nanofibers: A Magnetic Recyclable Catalyst for One-Pot Reductive Amination of Carbonyl Compound. Catalysis Letters 144:12, pages 2210-2215.
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Anastasiya S. Sokolova, Оlga I. Yarovaya, Dina V. Korchagina, Vladimir V. Zarubaev, Tatiana S. Tretiak, Pavel M. Anfimov, Oleg I. Kiselev & Nariman F. Salakhutdinov. (2014) Camphor-based symmetric diimines as inhibitors of influenza virus reproduction. Bioorganic & Medicinal Chemistry 22:7, pages 2141-2148.
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N. Uday Kumar, B. Sudhakar Reddy, V. Prabhakar Reddy & Rakeshwar Bandichhor. (2012) Iron triflate catalyzed reductive amination of aldehydes using sodium borohydride. Tetrahedron Letters 53:33, pages 4354-4356.
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Giovanni B Giovenzana, Daniela Imperio, Andrea Penoni & Giovanni Palmisano. (2011) Reductive amination with zinc powder in aqueous media. Beilstein Journal of Organic Chemistry 7, pages 1095-1099.
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Nalluri Sanjeevakumar & Mariappan Periasamy. (2009) Highly enantioselective Henry reaction catalyzed by a new chiral C2-symmetric N,N′-bis(isobornyl)ethylenediamine–copper complex. Tetrahedron: Asymmetry 20:16, pages 1842-1847.
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Sefer Ay, Martin Nieger & Stefan Bräse. (2008) Co‐Metal‐Free Enantioselective Conjugate Addition Reactions of Zinc Reagents. Chemistry – A European Journal 14:36, pages 11539-11556.
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Najmedin Azizi, Elham Akbari, Alireza Khejeh Amiri & Mohammad R. Saidi. (2008) Highly chemoselective reductive amination-coupling by one-pot reaction of aldehydes, HMDS and NaBH4. Tetrahedron Letters 49:47, pages 6682-6684.
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Mariappan Periasamy, Maddali L. N. Rao, Javed Iqbal & T. Punniyamurthy. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Byung Tae Cho & Sang Kyu Kang. (2005) Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions. Tetrahedron 61:24, pages 5725-5734.
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Takeshi Takeda, Yasutaka Yatsumonji & Akira Tsubouchi. (2005) Titanocene(II)-promoted reductive alkylation of anilides with thioacetals. Tetrahedron Letters 46:18, pages 3157-3160.
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Alessandro Caselli, Giovanni B. Giovenzana, Giovanni Palmisano, Massimo Sisti & Tullio Pilati. (2003) Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naphthols. Tetrahedron: Asymmetry 14:11, pages 1451-1454.
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Juan C. Jaen. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Mariappan Periasamy & Maddali L. N. Rao. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Thomas J. Caggiano. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Carl A. Busacca, Scot Campbell, Yong Dong, Danja Grossbach, Mike Ridges, Lana Smith & Earl Spinelli. (2000) Stereoselective Synthesis of (1 R ,2 S ,3 R )-Camphordiamine . The Journal of Organic Chemistry 65:15, pages 4753-4755.
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Matthias Beller & Carsten BolmBakthan Singaram & Christian T. Goralski. 1998. Transition Metals for Organic Synthesis. Transition Metals for Organic Synthesis 147 154 .
Sanjay Talukdar & Asoke Banerji. (1998) Low Valent Titanium Mediated Imino−Pinacol Coupling:  An Improved and Expeditious Route to Vicinal Diamino-Based Ligands. The Journal of Organic Chemistry 63:10, pages 3468-3470.
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M.Lakshmi Narayana Rao & Mariappan Periasamy. (1998) The CoCl2/Ph(Et)2N:BH3/CO system: Reactions of the borane and cobalt carbonyl species. Journal of Organometallic Chemistry 553:1-2, pages 91-97.
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. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1103 1295 .
C.M. Marson & A.D. Hobson. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 297 332 .
Joseph C. Fuller, Christopher M. Belisle, Christian T. Goralski & Bakthan Singaram. (1994) Aminoborohydrides. 6. Diastereoselective reduction of the carbon-nitrogen double bond in chiral imines using lithium diethylaminoborohydride and lithium diisopropylaminoborohydride. Tetrahedron Letters 35:30, pages 5389-5392.
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Roger Bolton, Timothy N. Danks & Jane M. Paul. (1994) Preparation and reduction of some camphor imines. Tetrahedron Letters 35:20, pages 3411-3412.
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Li ShengJian, Jiang Yaozhong & Mi Aiqiao. (1992) Asymmetric synthesis XVII. New chiral catalysts for the stereocontrolled addition of benzaldehyde by diethylzinc. Tetrahedron: Asymmetry 3:11, pages 1467-1474.
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. 1992. Compendium of Organic Synthetic Methods. Compendium of Organic Synthetic Methods 141 164 .
László Markó. (1991) Transition metals in organic synthesis: hydroformylation, reduction, and oxidation. Journal of Organometallic Chemistry 404:1-3, pages 325-504.
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M. PERIASAMY, A. DEVASAGAYARAJ, N. SATYANARAYANA & C. NARAYANA. (2016) ChemInform Abstract: Synthesis of Amines by Reduction of Imines with the MCl2/NaBH4 (M = Co, Ni) System.. ChemInform 20:51.
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