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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 15
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Original Articles

An Efficient Synthesis of Diethyl 1-Aminoalkylphosphonate Hydrochlorides via the Intermediate Diethyl 1-Azidoalkylphosphonates

Tadeusz Gajda Institute of Organic Chemistry Technical University, Zwirki 36, 90-924, Lódź, Poland
&
Maciej Matusiak Institute of Organic Chemistry Technical University, Zwirki 36, 90-924, Lódź, Poland
Pages 2193-2203 | Received 30 Mar 1992, Published online: 24 Sep 2006

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Roman Błaszczyk & Tadeusz Gajda. (2008) Convenient Synthesis of Dialkyl 1‐Azidoalkylphosphonates using Tetramethylguanidinium Azide as Azidation Agent. Synthetic Communications 38:7, pages 1110-1119.
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Babak Kaboudin & Abbas Rahmani. (2004) CONVENIENT SYNTHESIS OF 1-AMINOALKYLPHOSPHONATES UNDER SOLVENT-FREE CONDITIONS. Organic Preparations and Procedures International 36:1, pages 82-86.
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Denghuang Gong, Ling Zhang & Chengye Yuan. (2004) A Novel Route to 3‐(O,O‐Diethylphosphoryl)‐2,3‐dihydrofurans via Rhodium‐Catalyzed Heterocycloaddition Reaction. Synthetic Communications 34:18, pages 3251-3258.
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Dae Young Kim, Ki Hyung Suh, Sun Chul Huh & Kilsung Lee. (2001) MICHAEL ADDITION OF N-(DIPHENYLMETHYLENE)- AMINOMETHYLPHOSPHONATE TO ACRYLATES USING PHASE TRANSFER CATALYSIS CONDITIONS: SYNTHESIS OF 1-(N-DIPHENYLMETHYLENE)AMINO- 3-(ALKOXYCARBONYL)- PROPYLPHOSPHONATES. Synthetic Communications 31:21, pages 3315-3322.
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Yong Ye, Qiang Zeng & Lun-Zu Liu. (2001) THE SYNTHESIS OF N-(β-TRIPHENYLGERMANYL)-PROPIONYL-α-AMINOBENZYLPHOSPHONATES. Synthetic Communications 31:15, pages 2373-2378.
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Jiaxi Xu & Ming Wei. (2001) A CONVENIENT METHOD FOR THE SYNTHESIS OF N-PROTECTED 1-AMINOALKYLPHOSPHONATE MIXED MONOTHIOESTERS AND DITHIOESTERS. Synthetic Communications 31:10, pages 1489-1497.
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D. Sikora & T. Gajda. (2000) A FACILE SYNTHESIS OF DIETHYL 1- ISOTHIOCYANO)ALKYLPHOSPHONATES[1] . Phosphorus, Sulfur, and Silicon and the Related Elements 157:1, pages 201-210.
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Dorota Sikora & Tadeusz Gajda. (1998) A Convenient Synthesis of 5-Substituted 1 -[1 -(Diethoxyphosphoryl)alkyl]-1 H-1, 2, 3-triazoles. Synthetic Communications 28:7, pages 1215-1222.
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T. Gajda, M. Nowalinska, S. Zawadzki & A. Zwierzak. (1995) NEW APPROACH TO DIETHYL 2-AMINOALKYLPHOSPHONATES. Phosphorus, Sulfur, and Silicon and the Related Elements 105:1-4, pages 45-50.
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A. Elachqar, A. El Hallaouiq, M.L. Roumestant & Ph. Viallefont. (1994) Synthesis of Heterocyclic α-Aminophosphonic Acids. Synthetic Communications 24:9, pages 1279-1286.
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Tadeusz Gajda. (1993) A CONVENIENT SYNTHESIS OF O-ETHYL-1-AMINOALKYLPHOSPHINATES. Phosphorus, Sulfur, and Silicon and the Related Elements 85:1-4, pages 59-64.
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Bathélémy Ngameni, Musa Erdoğan, Victor Kuete, Erdin Dalkılıç, Bonaventure T Ngadjui & Arif Daştan. (2020) Synthesis and structural characterization of novel O -substituted phenolic and chalcone derivatives with antioxidant activity . Journal of Chemical Research 45:1-2, pages 159-165.
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Chandra S. Kuruva, Syam P. Gandavaram, Venkata S. Kadiam, Lokanatha Valluru & Naga R. Chamarthi. (2018) Synthesis of New Heteroaryl α‐Aminophosphonates and Evaluation of Their Cytotoxicity against Human Breast Cancer MCF‐7 Cell Lines. ChemistrySelect 3:23, pages 6479-6487.
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Robert E. Furlani, Andrew A. Yeagley & Christian Melander. (2013) A flexible approach to 1,4-di-substituted 2-aminoimidazoles that inhibit and disperse biofilms and potentiate the effects of β-lactams against multi-drug resistant bacteria. European Journal of Medicinal Chemistry 62, pages 59-70.
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Qiuli Yao & Chengye Yuan. (2012) Stereospecific Transformation of Protected P–H Group into P–O or P–N Group in One-Pot Reaction. The Journal of Organic Chemistry 77:23, pages 10985-10990.
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Robert Engel & JaimeLee Iolani Cohen. 2011. Encyclopedia of Inorganic and Bioinorganic Chemistry. Encyclopedia of Inorganic and Bioinorganic Chemistry.
Mateusz Psurski, Katarzyna Błażewska, Anna Gajda, Tadeusz Gajda, Joanna Wietrzyk & Józef Oleksyszyn. (2011) Synthesis and antiproliferative activity of novel α- and β-dialkoxyphosphoryl isothiocyanates. Bioorganic & Medicinal Chemistry Letters 21:15, pages 4572-4576.
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Sara Sobhani & Zahra Tashrifi. (2010) Synthesis of α-functionalized phosphonates from α-hydroxyphosphonates. Tetrahedron 66:7, pages 1429-1439.
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R. S. Edmundson. 2009. PATAI'S Chemistry of Functional Groups. PATAI'S Chemistry of Functional Groups.
You-Ping Tian, Feng Xu, Yi Wang, Jian-Jun Wang & Hui-Li Li. (2009) PPh 3 -catalysed One-Pot Three-Component Syntheses of α-aminophosphonates under Solvent-Free Conditions . Journal of Chemical Research 2009:2, pages 78-80.
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Sara Sobhani & Zahra Tashrifi. (2009) One‐pot synthesis of primary 1‐aminophosphonates: Coupling reaction of carbonyl compounds, hexamethyldisilazane, and diethyl phosphite catalyzed by Al(OTf) 3 . Heteroatom Chemistry 20:2, pages 109-115.
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Francisco Palacios, Concepción Alonso, Domitila Aparicio, Gloria Rubiales & Jesús M. de los Santos. (2007) The aza-Wittig reaction: an efficient tool for the construction of carbon–nitrogen double bonds. Tetrahedron 63:3, pages 523-575.
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Yomadis A. Ortiz Barbosa, David J. Hart & Nabi A. Magomedov. (2006) Spiroquinazoline support studies: methods for the preparation of imidazoloindolines from oxindoles. Tetrahedron 62:37, pages 8748-8754.
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David Crich, Michio Shirai, Franck Brebion & Sochanchingwung Rumthao. (2006) Enantioselective alkene radical cations reactions. Tetrahedron 62:27, pages 6501-6518.
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Robert Engel & JaimeLee Iolani Cohen. 2006. Encyclopedia of Inorganic Chemistry. Encyclopedia of Inorganic Chemistry.
Babak Kaboudin & Khavar Moradi. (2005) A simple and convenient procedure for the synthesis of 1-aminophosphonates from aromatic aldehydes. Tetrahedron Letters 46:17, pages 2989-2991.
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Chengfu Xu & Chengye Yuan. (2004) A Facile Synthesis of Optically Active ?-Amino-?-arylethylphosphonates by Mitsunobu Reaction. European Journal of Organic Chemistry 2004:21, pages 4410-4415.
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Habib Firouzabadi, Nasser Iranpoor & Sara Sobhani. (2004) PPh3/DDQ as a neutral system for the facile preparation of diethyl α-bromo, α-iodo and α-azidophosphonates from diethyl α-hydroxyphosphonates. Tetrahedron 60:1, pages 203-210.
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Chengye Yuan, Chengfu Xu & Yonghui Zhang. (2003) Enzymatic synthesis of optically active 1- and 2-aminoalkanephosphonates. Tetrahedron 59:32, pages 6095-6102.
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Katarzyna Błażewska & Tadeusz Gajda. (2002) ( S )-Naproxen® and ( S )-Ibuprofen® chlorides—convenient chemical derivatizing agents for the determination of the enantiomeric excess of hydroxy and aminophosphonates by 31 P NMR. Tetrahedron: Asymmetry 13:7, pages 671-674.
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Ralph N. Salvatore, Cheol Hwan Yoon & Kyung Woon Jung. (2001) Synthesis of secondary amines. Tetrahedron 57:37, pages 7785-7811.
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Dorota Sikora & Tadeusz Gajda. (2000) A New Synthesis of Protected Phosphonodipeptides with an N-Terminal Amino Acid. Tetrahedron 56:23, pages 3755-3761.
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Roman Gancarz, Rafał Latajka, Beata Małuszek, Ewa Żymańczyk-Duda & Paweł Kafarski. (2000) Hydrogen bonding in diethyl 2-hydroxypropylphosphonate-an example of equilibrium between intramolecular and intermolecular bonding. Magnetic Resonance in Chemistry 38:3, pages 197-200.
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Jiaxi Xu, Yuan Ma & Lifang Duan. (2000) A novel synthetic route to N-protected 1-aminoalkylphosphonates. Heteroatom Chemistry 11:6, pages 417-421.
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Dorota Sikora & Tadeusz Gajda. (1998) A new approach to the synthesis of functionalized 1-alkenyl-1H-1,2,3-triazoles. Tetrahedron 54:10, pages 2243-2250.
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Dae Young Kim & Dae Yong Rhie. (1997) Synthesis of α-aminoalkylphosphonates from vinylphosphonates via aziridinylphosphonates. Tetrahedron 53:40, pages 13603-13608.
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A.R Sardarian*B Kaboudin. (1997) A Novel Synthesis of Diethyl 1-Aminoarylmethylphosphonates on the Surface of Alumina. Tetrahedron Letters 38:14, pages 2543-2546.
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Donovan Green, Said Elgendy, Geeta Patel, Jehan A. Baban, Emmanuel Skordalakes, Wahid Husman, Vijay V. Kakkar & John Deadman. (1996) The facile synthesis of O,O-Dialkyl α-halobenzylphosphonates from O,O-Dialkyl α-hydroxybenzylphosphonates. Tetrahedron 52:30, pages 10215-10224.
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Ewa Żymańczyk-Duda, Barbara Lejczak, Pawel Kafarski, Jean Grimaud & Peter Fischer. (1995) Enantioselective reduction of diethyl 2-oxoalkylphosphonates by baker's yeast. Tetrahedron 51:43, pages 11809-11814.
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Tu‐Chen Lin, Ming‐Chu Cheng, Shie Ming Peng, Shiuh‐Tzung Liu & Fu‐Mei Kiang. (2013) Reactivity of Iminophosphoranes. Formation of the Piperazine Ring. Journal of the Chinese Chemical Society 42:3, pages 543-546.
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Tadeusz Gajda. (1994) Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalyzed borane reduction of diethyl α-ketophosphonates. Tetrahedron: Asymmetry 5:10, pages 1965-1972.
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Martin J. O'Donnell, Linda K. Lawley, Pradeep B. Pushpavanam, Alain Burger, F.G. Bordwell & Xian-Man Zhang. (1994) Preparation of an α-aminophosphonate cation equivalent and its reaction with organoboranes. Tetrahedron Letters 35:35, pages 6421-6424.
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T. GAJDA & M. MATSIAK. (2010) ChemInform Abstract: An Efficient Synthesis of Diethyl 1‐Aminoalkylphosphonate Hydrochlorides via the Intermediate Diethyl 1‐Azidoalkylphosphonates.. ChemInform 24:6.
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