One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina

被引：99
|
作者：
Ambica [1 ]
Kumar, Satish [1 ]
Taneja, Subhash C. [2 ]
Hundal, Maninder S. [3 ]
Kapoor, Kamal K. [1 ]
机构：
[1] Univ Jammu, Dept Chem, Jammu 180006, India
[2] Indian Inst Integrat Med, Bioorgan Chem Div, Jammu 180001, India
[3] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 14期
关键词：
sbCl(3)/Al2O3; alpha-amino acid; alpha-aminophosphonate; solid supported reagents; recyclability;
D O I：
10.1016/j.tetlet.2008.02.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
SbCl3 adsorbed on Al2O3 is found to be an efficient and recyclable catalyst in promoting three-component coupling reactions of aldehydes (aromatic and aliphatic), amines (aryl amines, aliphatic amines and esters of S-cc-amino acids) and dialkylphosphites to afford the corresponding alpha-aminophosphonates in high yields. The ethyl ester of S-phenylalanine was observed to yield the corresponding ot-aminophosphonate with S,S-diastereoisomer formed in dominance over the S,R-diastereoisomer. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2208 / 2212
页数：5
相关论文
共 50 条
  • [21] Tetramethylguanidine (TMG)-catalysed synthesis of α-aminophosphonates by a one-pot reaction
    Sankar, Arigala Uma Ravi
    Kumar, B. Siva
    Raju, C. Naga
    Reddy, C. Suresh
    SOUTH AFRICAN JOURNAL OF CHEMISTRY-SUID-AFRIKAANSE TYDSKRIF VIR CHEMIE, 2007, 60 : 125 - 128
  • [22] An Efficient Organocatalysis: A One-Pot Highly Enantioselective Synthesis of -Aminophosphonates
    Thorat, Prashant B.
    Goswami, Santosh V.
    Magar, Rupali L.
    Patil, Bhagwan R.
    Bhusare, Sudhakar R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5509 - 5516
  • [23] Titanocene Dichloride as an Efficient Catalyst for One-Pot Synthesis of α-Aminophosphonates
    Niu, Hong-Ying
    Li, Hui-Juan
    Li, Jian-Ping
    Huang, Yu
    Mao, Run-Ze
    Li, De-Yang
    Qu, Gui-Rong
    Guo, Hai-Ming
    LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (09) : 674 - 681
  • [24] GRAPHENE OXIDE AS RECYCLABLE CATALYST FOR ONE-POT SYNTHESIS OF α-AMINOPHOSPHONATES
    Dhopte, Kiran B.
    Raut, Dnyaneshwar S.
    Patwardhan, Anand V.
    Nemade, Parag R.
    SYNTHETIC COMMUNICATIONS, 2015, 45 (06) : 788 - 798
  • [25] Metal triflate-catalyzed one-pot synthesis of α-aminophosphonates from carbonyl compounds in the absence of solvent
    Firouzabadi, H
    Iranpoor, N
    Sobhani, S
    SYNTHESIS-STUTTGART, 2004, (16): : 2692 - 2696
  • [26] Antimony (III) Sulfate Catalyzed One-Pot Synthesis of 2,3-Disubstitutedindoles
    Srinivasa, A.
    Mahadevan, K. M.
    Varma, P. Prabhakara
    Sudhakara, A.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (07) : 1843 - 1853
  • [27] Catalyst free one-pot synthesis of -aminophosphonates in aqueous ethyl lactate
    Gao, Ge
    Chen, Meng-Nan
    Mo, Li-Ping
    Zhang, Zhan-Hui
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (4-6) : 528 - 532
  • [28] One-Pot Synthesis and Antimicrobial Activity of Novel α-Aminophosphonates Using TMG
    Kumar, B. Siva
    Reddy, Y. Haranadha
    Rani, C. Radha
    Reddy, G. Chnadra Sekhar
    E-JOURNAL OF CHEMISTRY, 2011, 8 : S137 - S142
  • [29] DESIGN AND ONE-POT SYNTHESIS OF α-AMINOPHOSPHONATES AND BIS(α-AMINOPHOSPHONATES) BY IRON (III) CHLORIDE AND CYTOTOXIC ACTIVITY
    Rezaei, Zahra
    Firouzabadi, Habib
    Iranpoor, Nasser
    Ghaderi, Abbas
    Jafari, Mohammad Reza
    Jafari, Abbas Ali
    Zare, Hamid Reza
    DRUGS OF THE FUTURE, 2009, 34 : 65 - 65
  • [30] Design and one-pot synthesis of α-aminophosphonates and bis (α-aminophosphonates) by iron(III) chloride and cytotoxic activity
    Rezaei, Zahra
    Firouzabadi, Habib
    Iranpoor, Nasser
    Ghaderi, Abbas
    Jafari, Mohammad Reza
    Jafari, Abbas Ali
    Zare, Hamid Reza
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (11) : 4266 - 4275
12345