Niobium pentoxide, a recyclable heterogeneous solid surface catalyst for the synthesis of α-amino phosphonates

Abstract

Niobium pentoxide, a bifunctional solid surface catalyst, has been successfully employed to facilitate the three-component reaction between aldehydes, amines and triethyl phosphite at room temperature under solvent-free conditions to generate α-amino phosphonate in moderate to good yields. The catalyst can be recycled through simple filtration and reused to effect this transformation.

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References

  1. 1.

    (a) Engberts J B F N, Feringn B L, Keller E and Otto S 1996 Lewis‐acid catalysis of carbon carbon bond forming reactions in water Recl. Trav. Chim. 115 457; (b) Yamamoto H Lewis Acids in Organic Synthesis Vol. 1 (Weinheim, Germany: Wiley-VCH Verlag GmbH)

  2. 2.

    (a) Hou J T, Gao J W and Zhang Z H 2011 NbCl5: an efficient catalyst for one-pot synthesis of α-aminophosphonates under solvent-free conditions Appl. Organometal. Chem. 25 47; (b) Maghsoodlou M T, Habibi-Khorassani S M, Heydari R, Hazeri N, Sajadikhah S S and Rostamizadeh M 2010 Al(H2PO4)3 as an efficient and reusable catalyst for one‐pot three‐component synthesis of α‐amino phosphonates under solvent‐free conditions Chin. J. Chem. 28 285; (c) Gallardo-Macias R and Nakayama K 2010 Tin(II) compounds as catalysts for the Kabachnik-Fields reaction under solvent-free conditions: Facile synthesis of α-aminophosphonates Synthesis 57; (d) Rezaei Z, Firouzabadi H, Iranpoor N, Ghaderi A, Jafari M R, Jafari A A and Zare H R 2009 Design and one-pot synthesis of alpha-aminophosphonates and bis(alpha-aminophosphonates) by iron(III) chloride and cytotoxic activity Eur. J. Med. Chem. 44 4266; (e) Sobhani S and Tashrifi Z 2009 Al(OTf)3 as an efficient catalyst for one-pot synthesis of primary diethyl 1-aminophosphonates under solvent-free conditions Synth. Commun. 39 120; (f) Sobhani S and Tashrifi Z 2009 One‐pot synthesis of primary 1‐aminophosphonates: Coupling reaction of carbonyl compounds, hexamethyldisilazane, and diethyl phosphite catalyzed by Al(OTf)3 Heteroat. Chem. 20 109; (g) Bhagat S and Chakraborti A K 2007 An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik−Fields reaction) for the synthesis of α-amino phosphonates catalyzed by magnesium perchlorate J. Org. Chem. 72 1263; (h) Xu F, Luo Y Q, Wu J T, Shen Q and Chen H 2006 Facile one‐pot synthesis of α‐amino phosphonates using lanthanide chloride as catalyst Heteroat. Chem. 17 389; (i) Zhan Z P and Li J P 2005 Bismuth (III) chloride–catalyzed three‐component coupling: Synthesis of α‐amino phosphonates Synth. Commun. 35 2501; (j) Ghosh R, Maiti S, Chakraborty A and Maiti D K 2004 In(OTf)3 catalysed simple one-pot synthesis of α-amino phosphonates J. Mol. Catal. A: Chem. 210 53; (k) Azizi N and Saidi M R 2003 Lithium perchlorate‐catalyzed three‐component coupling: A facile and general method for the synthesis of α‐aminophosphonates under solvent‐free conditions Eur. J. Org. Chem. 4630; (l) Ranu B C, Hajra A and Jana U 1999 General procedure for the synthesis of α-amino phosphonates from aldehydes and ketones using indium (III) chloride as a catalyst Org. Lett. 1 1141; (m) Bhagat S and Chakraborti A K 2008 Zirconium (IV) compounds as efficient catalysts for synthesis of α-aminophosphonates J. Org. Chem. 73 6029; (n) Kasthuraiah M, Kumar K A, Reddy C S and Reddy C D 2007 Syntheses, spectral property, and antimicrobial activities of 6‐α‐amino dibenzo [d,f][1,3,2]dioxaphosphepin 6‐oxides Heteroat. Chem. 18 2; (o) Xu F, Luo Y Q, Deng M Y and Shen Q 2003 One‐pot synthesis of α‐amino phosphonates using samarium diiodide as a Catalyst Precursor Eur. J. Org. Chem. 4728; (p) Chandrasekhar S, Prakash S J, Jagadeshwar V and Narsihmulu C 2001 Three component coupling catalyzed by TaCl5–SiO2: synthesis of α-amino phosphonates Tetrahedron Lett. 42 5561; (q) Ambica, Kumar S, Taneja S C, Hundal M S and Kapoor K K 2008 One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina Tetrahedron Lett. 49 2208; (r) Cherkasov R A and Galkin V I 1998 The Kabachnik–Fields reaction: synthetic potential and the problem of the mechanism Russ. Chem. Rev. 67 857; (s) Abdel-Rahman R M, Ali T E and Abdel-Kariem S M 2016 Methods for synthesis of N-heterocyclyl/heteroaryl- α-aminophosphonates and α-(azaheterocyclyl)phosphonates Arkivoc. 183

  3. 3.

    Bekkum H V and Kouwenhoven H W 2007 Introduction to Zeolite Science and Practice Jiri Cejka, Herman van Bekkum, Avelino Corma and Ferdi Schuth (Eds.) (Amsterdam: Elsevier) Vol. 168, pp. 947–997

  4. 4.

    Gawande M B, Pandey R K and Jayaram R V 2012 Role of mixed metal oxides in catalysis science-versatile applications in organic synthesis J. Catal. Sci. Technol. 2 1113

    CAS  Article  Google Scholar 

  5. 5.

    (a) Varma R S 2002 Clay and clay-supported reagents in organic synthesis Tetrahedron 58 1235; (b) Dasgupta S and Torok B 2009 Application of clay catalysts in organic synthesis. A review Org. Prep. Proced. Int. 40 1

  6. 6.

    Kozhevnikov I V 1994 Heteropoly Acids as Catalysts for Organic Reactions Stud. Surf. Sci. Catal. 90 21

    CAS  Article  Google Scholar 

  7. 7.

    Siddiki S M A H, Rashed M N, Ali M A, Toyao T, Hirunsit P, Ehara M and Shimizu K 2019 Lewis acid catalysis of Nb2O5 for reactions of carboxylic acid derivatives in the presence of basic inhibitors ChemCatChem. 11 383

  8. 8.

    Yang S, Gao X -W, Diao C L, Song B -A, Jin L -H, Xu G -F, Zhang G -P, Wang W, Hu D -Y, Xue W, Zhou X and Lu P 2006 Synthesis and antifungal activity of novel chiral α‐aminophosphonates containing fluorine moiety Chin. J. Chem. 24 1581

    CAS  Google Scholar 

  9. 9.

    Reddy G S, Rao K U M, Sundar C S, Sudha S S, Haritha B, Swapna S and Reddy C S 2014 Neat synthesis and antioxidant activity of a-aminophosphonates Arab. J. Chem. 7 833

    Google Scholar 

  10. 10.

    Dake S A, Raut D S, Kharat K R, Mhaske R S, Deshmukh S U and Pawar R P 2011 Ionic liquid promoted synthesis, antibacterial and in vitro antiproliferative activity of novel α-aminophosphonate derivatives Bioorg. Med. Chem. Lett. 21 2527

    CAS  Article  Google Scholar 

  11. 11.

    Sivala M R, Devineni S R, Golla M, Medarametla V, Pothuru G K and Chamarthi N R 2016 A heterogeneous catalyst, SiO2-ZnBr2: An efficient neat access for α-aminophosphonates and antimicrobial activity evaluation J. Chem. Sci. 128 1303

    CAS  Article  Google Scholar 

  12. 12.

    Ramana K V, Rasheed S, Sekhar K C, Adam S and Raju C N 2012 One-pot and catalyst-free synthesis of novel α-aminophosphonates under microwave irradiation and their biological activity Der Pharmacia Lett. 4 456

    CAS  Google Scholar 

  13. 13.

    Abdou W M, Barghash R F and Bekheit M S 2011 Multicomponent reactions in a one-pot synthesis of α-aminophosphonates and α-aminophosphonic diamides with anti-inflammatory properties Monatsh Chem. 142 649

    CAS  Google Scholar 

  14. 14.

    El-Boraey H A L, El-Gokha A A A, El-Soyad I E T and Azzam M A 2015 Transition metal complexes of α-aminophosphonates Part I: synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes of α-aminophosphonates Med. Chem. Res. 24 2142

    CAS  Google Scholar 

  15. 15.

    Lejczak B, Kafarski P and Gancarz R 1988 Plant growth regulating properties of 1‐amino‐1‐methylethylphosphonic acid and its derivatives Pestic. Sci. 22 263

    CAS  Article  Google Scholar 

  16. 16.

    Bhattacharya A K, Rana K C, Pannecouque C and Clercq E D 2012 An efficient synthesis of a hydroxyethylamine (HEA) isostere and its α‐aminophosphonate and phosphoramidate derivatives as potential anti‐HIV agents ChemMedChem 7 1601

  17. 17.

    Herrera R P and Marqués-López E 2015 Multicomponent reactions: Concepts and applications for design and synthesis (New Jersey: John Wiley & Sons) Ch. 12

    Google Scholar 

  18. 18.

    (a) Mangalaraj S and amanathan C R 2012 Construction of tetrahydro-b-carboline skeletons via Brønsted acid activation of imide carbonyl group: syntheses of indole alkaloids (±)-harmicine and (±)-10-desbromoarborescidine-A RSC Adv. 2 12665; (b) Selvakumar J, Rao R S, Srinivasapriyan V, Marutheeswaran S and Ramanathan C R 2015 Synthesis of condensed tetrahydroisoquinoline class of alkaloids by employing TfOH-mediated imide carbonyl activation Eur. J. Org. Chem. 2175; (c) Harikrishnan A, Sanjeevi J and Ramanathan C R 2015 The cooperative effect of Lewis pairs in the Friedel–Crafts hydroxyalkylation reaction: a simple and effective route for the synthesis of(±)-carbinoxamine Org. Biomol. Chem. 13 3633; (d) Venkatanna K, Kumar S Y, Karthick M, Padmanaban P and Ramanathan C R 2019 A chiral bicyclic skeleton-tethered bipyridine–Zn(OTf)2 complex as a Lewis acid: enantioselective Friedel–Crafts alkylation of indoles with nitroalkenes Org. Biomol. Chem. 17 4077

  19. 19.

    (a) Harikrishnan A, Sanjeevi J and Ramanathan C R 2015 The cooperative effect of Lewis pairs in the Friedel–Crafts hydroxyalkylation reaction: a simple and effective route for the synthesis of (±)-carbinoxamine Org. Biomol. Chem. 13 3633; (b) Harikrishnan A, Selvakumar J, Gnanamani E, Bhattacharya S and Ramanathan C R 2013 Friedel–Crafts hydroxyalkylation through activation of a carbonyl group using AlBr3: an easy access to pyridyl aryl/heteroaryl carbinols New J. Chem. 37 563; (c) Gnanamani E, Someshwar N, Sanjeevi J and Ramanathan C R 2014 Conformationally rigid chiral bicyclic skeleton-tethered bipyridine N,N’-dioxide as organocatalyst: Asymmetric ring opening of meso-epoxides Adv. Synth. Catal. 356 2219

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Acknowledgements

We thank the SERB, New Delhi for financial (Grant No. CRG/2019/002,960) support. AS acknowledges the UGC for the fellowship. We thank UGC-SAP, Department of Chemistry. We gratefully acknowledge the Department of Chemistry, Pondicherry University for HRMS facility (DST-FIST Sponsored); Central Instrumentation Facility, Pondicherry University for NMR and IR data.

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Correspondence to Chinnasamy Ramaraj Ramanathan.

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Sahani, A., Rao, R.S., Vadakkayil, A. et al. Niobium pentoxide, a recyclable heterogeneous solid surface catalyst for the synthesis of α-amino phosphonates. J Chem Sci 133, 4 (2021). https://doi.org/10.1007/s12039-020-01853-7

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Keywords

  • α-Amino phosphonates
  • Bifunctional catalyst
  • Niobium pentoxide
  • Kabachnik-fields reaction
  • Organophosphorus compounds