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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

Al(OTf)3 as an Efficient Catalyst for One-Pot Synthesis of Primary Diethyl 1-Aminophosphonates Under Solvent-Free Conditions

Sara Sobhani Department of Chemistry, College of Sciences, Birjand University, Birjand, IranCorrespondence[email protected], [email protected]
&
Zahra Tashrifi Department of Chemistry, College of Sciences, Birjand University, Birjand, Iran
Pages 120-131 | Received 12 Jun 2008, Published online: 15 Feb 2011

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Mohan Gundluru, Santhisudha Sarva, Sumithra Poreddy, Poojitha B, Ashwini John, Selvarajan Ethiraj & Suresh Reddy Cirandur. (2023) Design, synthesis, antibacterial evaluation, and molecular docking studies of diethyl((substituted phenyl)((4-(N-(5-methyl-4,5-dihydroisoxazol-3-yl)sulfamoyl)phenyl) amino)methyl)phosphonates. Synthetic Communications 53:24, pages 2117-2133.
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Yasmin Haroon Shaik, Venkataramaiah Chintha, Mohan Gundluru, Santhisudha Sarva & Suresh Reddy Cirandur. (2022) An efficient nano-FGT catalyzed green synthesis of α-aminophosphonates and evaluation of their antioxidant, anti-inflammatory activity and molecular docking studies. Synthetic Communications 52:1, pages 129-144.
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Mozhgan Afshari, Maryam Gorjizadeh & Mohammad Naseh. (2017) Supported sulfonic acid on magnetic nanoparticles used as a reusable catalyst for rapid synthesis of α-aminophosphonates. Inorganic and Nano-Metal Chemistry 47:4, pages 591-596.
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Xing Wang, Yuan Cai, Jian Chen & Francis Verpoort. (2016) A simple protocol for the synthesis of α-substituted phosphonates. Phosphorus, Sulfur, and Silicon and the Related Elements 191:9, pages 1268-1273.
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Dong Fang, Yanfang Cao & Jinming Yang. (2013) Clean Procedure for the Synthesis of α-Aminophosphonates Catalyzed by Biodegradable Ionic Liquid. Phosphorus, Sulfur, and Silicon and the Related Elements 188:7, pages 826-832.
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Sara Sobhani & Soodabeh Rezazadeh. (2010) Michael Addition Reaction of Thioacetic Acid (AcSH) to Conjugated Alkenes Under Solvent- and Catalyst-Free Conditions. Phosphorus, Sulfur, and Silicon and the Related Elements 185:10, pages 2076-2084.
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Articles from other publishers (43)

E. R. Shakurova & L. V. Parfenova. Three-component synthesis of aminophosphonates based on phenylenediamines. Three-component synthesis of aminophosphonates based on phenylenediamines.
Zahra Tashrifi, Mohammad Mohammadi Khanaposhtani, Bagher Larijani & Mohammad Mahdavi. (2021) Sodium Azide: An Inorganic Nitrogen Source for the Synthesis of Organic N ‐Compounds . ChemistrySelect 6:47, pages 13419-13433.
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Sarfaraz Shaikh, Ishita Yellapurkar & M. M. V. Ramana. (2021) Ultrasound assisted one-pot synthesis of novel antipyrine based α-aminophosphonates using TiO2/carbon nanotubes nanocomposite as a heterogeneous catalyst. Reaction Kinetics, Mechanisms and Catalysis 134:2, pages 917-936.
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Anita Sahani, Ramana Sreenivasa Rao, Adithya Vadakkayil, Murugesan Santhosh, Mahalingam Mummoorthi, Muthupandi Karthick & Chinnasamy Ramaraj Ramanathan. (2021) Niobium pentoxide, a recyclable heterogeneous solid surface catalyst for the synthesis of α-amino phosphonates. Journal of Chemical Sciences 133:1.
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Bo Zhang, Xiu-Ting Hu, Jin Gu, Yu-Shun Yang, Yong-Tao Duan & Hai-Liang Zhu. (2020) Discovery of novel sulfonamide-containing aminophosphonate derivatives as selective COX-2 inhibitors and anti-tumor candidates. Bioorganic Chemistry 105, pages 104390.
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Bo Zhang, Xiu-Ting Hu, Kang-Min Zhou, Yu-Shun Yang & Hai-Liang Zhu. (2020) Discovery of novel aminophosphonate derivatives containing pyrazole moiety as potential selective COX-2 inhibitors. Bioorganic Chemistry 102, pages 104096.
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Murali Sudileti, Mohan Gundluru, Santhisudha Sarva, Sreekanth Tellamekala, Balaji Hari, Balaji Meriga & Suresh Reddy Cirandur. (2019) Tungstosulfonic acid-catalyzed green synthesis and bioassay of α-aminophosphonates. Monatshefte für Chemie - Chemical Monthly 150:6, pages 1101-1109.
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Samia Guezane‐Lakoud, Martial Toffano & Louisa Aribi‐Zouioueche. (2017) Promiscuous lipase catalyzed a new P–C bond formation: Green and efficient protocol for one‐pot synthesis of α‐aminophosphonates. Heteroatom Chemistry 28:6.
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Reddi Mohan Naidu Kalla, Jaeyeong Bae & Il Kim. (2017) Catalyst-free ultrasonic-promoted multicomponent synthesis of tertiary α-amino phosphonates. New Journal of Chemistry 41:14, pages 6653-6660.
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MUNICHANDRA REDDY SIVALA, SUBBA RAO DEVINENI, MADHAVA GOLLA, VENKATESH MEDARAMETLA, GNANA KUMARI POTHURU & NAGA RAJU CHAMARTHI. (2016) A heterogeneous catalyst, SiO2-ZnBr2: An efficient neat access for α-aminophosphonates and antimicrobial activity evaluation. Journal of Chemical Sciences 128:8, pages 1303-1313.
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Abdelkader Hellal, Salah Chafaa & Lasnouni Touafri. (2016) An eco-friendly procedure for the efficient synthesis of diethyl α-aminophosphonates in aqueous media using natural acids as a catalyst. Korean Journal of Chemical Engineering 33:8, pages 2366-2373.
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H. Betul Bingol, Ayse Altin, Tugba Bal, Sesil Agopcan‐Cinar, Seda Kizilel & Duygu Avci. (2015) Synthesis and evaluation of new phosphonic acid‐functionalized acrylamides with potential biomedical applications. Journal of Polymer Science Part A: Polymer Chemistry 53:23, pages 2755-2767.
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Ya-Jun Li, Cai-Yi Wang, Man-Yi Ye, Gui-Yang Yao & Heng-Shan Wang. (2015) Novel Coumarin-Containing Aminophosphonatesas Antitumor Agent: Synthesis, Cytotoxicity, DNA-Binding and Apoptosis Evaluation. Molecules 20:8, pages 14791-14809.
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Eugenia Marqués‐López & Raquel P. Herrera. 2015. Multicomponent Reactions. Multicomponent Reactions 382 415 .
Biyun Su, Xiaoteng Li, Xudong Wang & Qianding Li. (2015) Efficient Microwave-Assisted Syntheses of A Series of Novel Mono(imino)pyrrolyl Compounds. HETEROCYCLES 91:10, pages 1955.
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Man-Yi Ye, Gui-Yang Yao, Ying-Ming Pan, Zhi-Xin Liao, Ye Zhang & Heng-Shan Wang. (2014) Synthesis and antitumor activities of novel α-aminophosphonate derivatives containing an alizarin moiety. European Journal of Medicinal Chemistry 83, pages 116-128.
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Ya-Jun Li, Man-Yi Ye, Ri-Zhen Huang, Gui-Yang Yao, Ying-Ming Pan, Zhi-Xin Liao & Heng-Shan Wang. (2013) Coumarin-containing aminophosphonates bridged with chiral side chain: synthesis and influence of chirality on cytotoxicity and DNA binding. Medicinal Chemistry Research 23:6, pages 3144-3156.
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Mathieu Lafantaisie, Thomas Galeandro-Diamant & Thierry Ollevier. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis 1 5 .
Ayse Altin, Burcin Akgun, Zeynep Sarayli Bilgici, Sebnem Begum Turker & Duygu Avci. (2014) Synthesis, photopolymerization, and adhesive properties of hydrolytically stable phosphonic acid-containing (meth)acrylamides. Journal of Polymer Science Part A: Polymer Chemistry 52:4, pages 511-522.
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Sara Sobhani, Zahra Mesbah Falatooni & Moones Honarmand. (2014) Synthesis of phosphoric acid supported on magnetic core–shell nanoparticles: a novel recyclable heterogeneous catalyst for Kabachnik–Fields reaction in water. RSC Advances 4:30, pages 15797.
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Gui-yang Yao, Man-yi Ye, Ri-zhen Huang, Ya-jun Li, Ying-ming Pan, Qing Xu, Zhi-Xin Liao & Heng-shan Wang. (2014) Synthesis and antitumor activities of novel rhein α-aminophosphonates conjugates. Bioorganic & Medicinal Chemistry Letters 24:2, pages 501-507.
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Xiao-Chao Huang, Meng Wang, Ying-Ming Pan, Gui-Yang Yao, Heng-Shan Wang, Xiao-Yan Tian, Jiang-Ke Qin & Ye Zhang. (2013) Synthesis and antitumor activities of novel thiourea α-aminophosphonates from dehydroabietic acid. European Journal of Medicinal Chemistry 69, pages 508-520.
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Xiao-Chao Huang, Meng Wang, Ying-Ming Pan, Xiao-Yan Tian, Heng-Shan Wang & Ye Zhang. (2013) Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives. Bioorganic & Medicinal Chemistry Letters 23:19, pages 5283-5289.
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Ayse Altin, Burcin Akgun, Ozlem Buyukgumus, Zeynep Sarayli Bilgici, Sesil Agopcan, Didar Asik, Havva Yagci Acar & Duygu Avci. (2013) Synthesis and photopolymerization of novel, highly reactive phosphonated-urea-methacrylates for dental materials. Reactive and Functional Polymers 73:9, pages 1319-1326.
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SARA SOBHANI, ZAHRA PAKDIN-PARIZI & RAZIEH NASSERI. (2013) Nano n-propylsulphonated γ-Fe2O3: A novel magnetically recyclable heterogeneous catalyst for the efficient synthesis of bis(pyrazolyl)methanes in water. Journal of Chemical Sciences 125:5, pages 975-979.
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Subba Rao Devineni, Srinivasulu Doddaga, Rajasekhar Donka & Naga Raju Chamarthi. (2013) CeCl3·7H2O-SiO2: Catalyst promoted microwave assisted neat synthesis, antifungal and antioxidant activities of α-diaminophosphonates. Chinese Chemical Letters 24:8, pages 759-763.
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Sara Sobhani & Moones Honarmand. (2013) Silica-Bonded 2-Hydroxyethylammonium Acetate as an Efficient and Recyclable Catalyst for the Synthesis of 2-Amino-4H-chromen-4-yl Phosphonates and β-Phosphonomalonates. Catalysis Letters 143:5, pages 476-485.
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Man-Yi Ye, Gui-Yang Yao, Jing-Chen Wei, Ying-Ming Pan, Zhi-Xin Liao & Heng-Shan Wang. (2013) Synthesis, Cytotoxicity, DNA Binding and Apoptosis of Rhein-Phosphonate Derivatives as Antitumor Agents. International Journal of Molecular Sciences 14:5, pages 9424-9439.
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Nellisara D. Shashikumar. (2013) Preparation of New α -Aminophosphonate Derivatives by Kabachnik-Fields Reaction Using a Recyclable Catalyst . Journal of Chemistry 2013, pages 1-8.
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Sara Sobhani & Roya Jahanshahi. (2013) Nano n-propylsulfonated γ-Fe2O3 (NPS-γ-Fe2O3) as a magnetically recyclable heterogeneous catalyst for the efficient synthesis of 2-indolyl-1-nitroalkanes and bis(indolyl)methanes. New Journal of Chemistry 37:4, pages 1009.
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Nataliya S. Goulioukina, Ilya A. Shergold, Grigorii N. Bondarenko, Mikhail M. Ilyin, Vadim A. Davankov & Irina P. Beletskaya. (2012) Palladium‐Catalyzed Asymmetric Hydrogenation of N ‐Hydroxy‐α‐imino Phosphonates Using Brønsted Acid as Activator: The First Catalytic Enantioselective Approach to Chiral N ‐Hydroxy‐α‐amino Phosphonates . Advanced Synthesis & Catalysis 354:14-15, pages 2727-2733.
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S. Sobhani & M. Honarmand. (2012) 5-Hydroxypentylammonium acetate as a reusable ionic liquid catalyzes tandem Knoevenagel-phospha-Michael reaction of aldehydes, malononitrile and phosphites. Journal of the Iranian Chemical Society 9:5, pages 661-669.
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Zhongqiang Zhou, Yaru Pei & Lamei Wu. (2012) [BPy]HSO 4 as an Efficient and Recyclable Catalyst for One-Pot Synthesis of -Aminophosphonates under Solvent-Free Conditions . Organic Chemistry International 2012, pages 1-6.
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Mario Ordóñez, Francisco J. Sayago & Carlos Cativiela. (2012) Synthesis of quaternary α-aminophosphonic acids. Tetrahedron 68:32, pages 6369-6412.
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Sara Sobhani & Zahra Pakdin Parizi. (2011) An eco-friendly procedure for one-pot synthesis of β-phosphonomalonates: micellar solution of sodium stearate catalyzes tandem Knoevenagel–phospha-Michael reaction of aldehydes, malonitrile, and phosphites in aqueous media. Tetrahedron 67:19, pages 3540-3545.
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Dong Fang, Jinming Yang & Chunjie Ni. (2010) Dicationic ionic liquids as recyclable catalysts for one‐pot solvent‐free synthesis of α‐aminophosphonates. Heteroatom Chemistry 22:1, pages 5-10.
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Jun‐Tao Hou, Jian‐Wu Gao & Zhan‐Hui Zhang. (2010) NbCl 5 : an efficient catalyst for one‐pot synthesis of α‐aminophosphonates under solvent‐free conditions . Applied Organometallic Chemistry 25:1, pages 47-53.
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Mladen Litvić, Ivana Večenaj, Zrinka Mikuldaš Ladišić, Marija Lovrić, Vladimir Vinković & Mirela Filipan-Litvić. (2010) First application of hexaaquaaluminium(III) tetrafluoroborate as a mild, recyclable, non-hygroscopic acid catalyst in organic synthesis: a simple and efficient protocol for the multigram scale synthesis of 3,4-dihydropyrimidinones by Biginelli reaction. Tetrahedron 66:19, pages 3463-3471.
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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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Dong Fang, Changmei Jiao & Chunjie Ni. (2010) SO 3 H‐functionalized ionic liquids catalyzed the synthesis of α‐aminophosphonates in aqueous media . Heteroatom Chemistry 21:7, pages 546-550.
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Abbas Ali Jafari, Mahshid Nazarpour & Mohammad Abdollahi‐Alibeik. (2010) CeCl 3 ·7H 2 O‐catalyzed one‐pot Kabachnik–Fields reaction: A green protocol for three‐component synthesis of α‐aminophosphonates . Heteroatom Chemistry 21:6, pages 397-403.
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Sara Sobhani & Asieh Vafaee. (2009) Efficient one-pot synthesis of β-hydroxyphosphonates: regioselective nucleophilic ring opening reaction of epoxides with triethyl phosphite catalyzed by Al(OTf)3. Tetrahedron 65:36, pages 7691-7695.
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Sara Sobhani & Zahra Tashrifi. (2009) ChemInform Abstract: Al(OTf) 3 as an Efficient Catalyst for One‐Pot Synthesis of Primary Diethyl 1‐Aminophosphonates under Solvent‐Free Conditions. . ChemInform 40:25.
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