메뉴 건너뛰기




Volumn 37, Issue 5, 2007, Pages 743-757

One-pot preparation of fluorinated α-aminoalkyl phosphonates under microwave irradiation and solvent-free conditions

Author keywords

aminoalkyl phosphonates; Anilines; Fluorinated aldehydes; Microwave; Solvent free

Indexed keywords

1 [(2 FLUOROPHENYL)AMINO] 1 (3 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(2 FLUOROPHENYL)AMINO] 1 (4 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(3 CHLOROPHENYL)AMINO] 1 (3 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(3 CHLOROPHENYL)AMINO] 1 (4 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(3 FLUOROPHENYL)AMINO] 1 (3 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(3 FLUOROPHENYL)AMINO] 1 (4 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(3,4 DIFLUOROPHENYL)AMINO] 1 (3 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(3,4 DIFLUOROPHENYL)AMINO] 1 (4 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 FLUOROPHENYL)AMINO] 1 (3 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 FLUOROPHENYL)AMINO] 1 (4 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 METHOXYPHENYL)AMINO] 1 (3 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 METHOXYPHENYL)AMINO] 1 (4 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 METHYLPHENYL)AMINO] 1 (2 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 METHYLPHENYL)AMINO] 1 (3 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 METHYLPHENYL)AMINO] 1 (PENTAFLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 NITROPHENYL)AMINO] 1 (3 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; 1 [(4 NITROPHENYL)AMINO] 1 (4 FLUOROPHENYL) O,O DIETHYLMETHANEPHOSPHONATE; ALDEHYDE; ANILINE DERIVATIVE; FLUORINE DERIVATIVE; PHOSPHATE; PHOSPHORAMIDIC ACID DERIVATIVE; SILICON DIOXIDE; SOLVENT; UNCLASSIFIED DRUG;

EID: 33847112851     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910601131411     Document Type: Article
Times cited : (15)

References (29)
  • 1
    • 2542556554 scopus 로고    scopus 로고
    • Catalytic asymmetric synthesis of α-amino phosphonates using enantioselective carbon-carbon bondforming reactions
    • (a) Kobayashi, S.; Kiyohara, H.; Nakamura, Y.; Matsubara, R. Catalytic asymmetric synthesis of α-amino phosphonates using enantioselective carbon-carbon bondforming reactions. J. Am. Chem. Soc. 2004, 126, 6558-6559;
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 6558-6559
    • Kobayashi, S.1    Kiyohara, H.2    Nakamura, Y.3    Matsubara, R.4
  • 2
    • 0026470783 scopus 로고
    • Studies on organophosphorus compounds, LXIII: A new and facile synthetic route to protected phosphondipeptides: A backbone for the formation of oligophosphonopeptides
    • (b) Yuan, C.; Chen, S. Studies on organophosphorus compounds, LXIII: A new and facile synthetic route to protected phosphondipeptides: A backbone for the formation of oligophosphonopeptides. Synthesis 1992, 1124-1128;
    • (1992) Synthesis , pp. 1124-1128
    • Yuan, C.1    Chen, S.2
  • 3
    • 0028579682 scopus 로고
    • Stereoselective synthesis of β-oxygenated α-hydroxy phosphonates by Lewis acid-mediated stereoselective hydrophosphonylation of α-benzyloxy aldehydes: An application to the synthesis of phosphonic acid analogs of oxyamino acids
    • (c) Yokomatsu, T.; Yoshida, Y.; Shibuya, S. Stereoselective synthesis of β-oxygenated α-hydroxy phosphonates by Lewis acid-mediated stereoselective hydrophosphonylation of α-benzyloxy aldehydes: An application to the synthesis of phosphonic acid analogs of oxyamino acids. J. Org. Chem. 1994, 59, 7930-7933.
    • (1994) J. Org. Chem , vol.59 , pp. 7930-7933
    • Yokomatsu, T.1    Yoshida, Y.2    Shibuya, S.3
  • 5
    • 0024409372 scopus 로고
    • Renin inhibitors: Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond
    • (a) Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. Renin inhibitors: Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond. J. Med. Chem. 1989, 32, 1652-1661;
    • (1989) J. Med. Chem , vol.32 , pp. 1652-1661
    • Allen, M.C.1    Fuhrer, W.2    Tuck, B.3    Wade, R.4    Wood, J.M.5
  • 6
    • 0023780644 scopus 로고
    • Synthesis of α- and γ-alkyl-substituted phosphinothricins: Potent new inhibitors of glutamine synthetase
    • (b) Logusch, E. W.; Walker, D. M.; McDonald, H. F.; Leo, G. C.; Grang, J. E. Synthesis of α- and γ-alkyl-substituted phosphinothricins: Potent new inhibitors of glutamine synthetase. J. Org. Chem. 1988, 53, 4069-4074.
    • (1988) J. Org. Chem , vol.53 , pp. 4069-4074
    • Logusch, E.W.1    Walker, D.M.2    McDonald, H.F.3    Leo, G.C.4    Grang, J.E.5
  • 8
    • 0027982561 scopus 로고
    • Peptide bond formation via catalytic antibodies: Synthesis of a noval phosphonate diester hapten
    • (b) Smith III, A. B.; Taylor, C. M.; Venkovic, S. J. Peptide bond formation via catalytic antibodies: Synthesis of a noval phosphonate diester hapten. Tetrahedron Lett. 1994, 37, 6853-6856.
    • (1994) Tetrahedron Lett , vol.37 , pp. 6853-6856
    • Smith III, A.B.1    Taylor, C.M.2    Venkovic, S.J.3
  • 10
    • 0026549026 scopus 로고
    • Carbohydrates as chiral templates: Stereoselective synthesis of (R)-and (S)- α-aminophosphonic acid derivatives
    • (b) Lashat, S.; Kunz, H. Carbohydrates as chiral templates: Stereoselective synthesis of (R)-and (S)- α-aminophosphonic acid derivatives. Synthesis 1992, 90-94.
    • (1992) Synthesis , pp. 90-94
    • Lashat, S.1    Kunz, H.2
  • 11
    • 0000170021 scopus 로고
    • The synthesis of esters of substituted amino phosphonic acids
    • Fields, E. K. The synthesis of esters of substituted amino phosphonic acids. J. Am. Chem. Soc. 1952, 74, 1528-1531.
    • (1952) J. Am. Chem. Soc , vol.74 , pp. 1528-1531
    • Fields, E.K.1
  • 12
    • 0001448816 scopus 로고
    • Asymmetric addition of tris(trimethylsilyl) phosphite to chiral aldimines
    • (a) Zon, J. Asymmetric addition of tris(trimethylsilyl) phosphite to chiral aldimines. Pol. J. Chem. 1981, 55, 643;
    • (1981) Pol. J. Chem , vol.55 , pp. 643
    • Zon, J.1
  • 13
    • 0034609148 scopus 로고    scopus 로고
    • β, γ-unsaturated α-aminophosphonates: Synthesis and reactivity
    • (b) Atmani, A.; Combret, J. C.; Malhiac, C.; Kajima Mulengi, J. β, γ-unsaturated α-aminophosphonates: Synthesis and reactivity. Tetrahedron Lett. 2000, 41, 6045-6048.
    • (2000) Tetrahedron Lett , vol.41 , pp. 6045-6048
    • Atmani, A.1    Combret, J.C.2    Malhiac, C.3    Kajima Mulengi, J.4
  • 14
    • 0032511117 scopus 로고    scopus 로고
    • One-pot synthesis of α-amino phosphonates from aldehydes using lanthanide triflate as a catalyst
    • (a) Qian, C. T.; Huang, T. S. One-pot synthesis of α-amino phosphonates from aldehydes using lanthanide triflate as a catalyst. J. Org. Chem. 1998, 63, 4125-4128;
    • (1998) J. Org. Chem , vol.63 , pp. 4125-4128
    • Qian, C.T.1    Huang, T.S.2
  • 15
    • 0035823302 scopus 로고    scopus 로고
    • Lanthanide triflatecatalyzed three-component synthesis of α-amino phosphonates in ionic liquids: A catalyst reactivity and reusability study
    • (b) Lee, S.; Park, J. H.; Kang, J.; Lee, J. K. Lanthanide triflatecatalyzed three-component synthesis of α-amino phosphonates in ionic liquids: A catalyst reactivity and reusability study. Chem. Commun. 2001, 1698-1699.
    • (2001) Chem. Commun , pp. 1698-1699
    • Lee, S.1    Park, J.H.2    Kang, J.3    Lee, J.K.4
  • 16
    • 0001641346 scopus 로고    scopus 로고
    • General procedure for the synthesis of α-amino phosphonates from aldehydes and ketones using indium(III) chloride as a catalyst
    • Ranu, B. C.; Hajra, A.; Jana, U. General procedure for the synthesis of α-amino phosphonates from aldehydes and ketones using indium(III) chloride as a catalyst. Org. Lett. 1999, 1, 1141-1143.
    • (1999) Org. Lett , vol.1 , pp. 1141-1143
    • Ranu, B.C.1    Hajra, A.2    Jana, U.3
  • 17
    • 0034696904 scopus 로고    scopus 로고
    • Facile synthesis of a-amino phosphonates in water using a Lewis acid-surfactant combined catalyst
    • Manabe, K.; Kobayashi, S. Facile synthesis of a-amino phosphonates in water using a Lewis acid-surfactant combined catalyst. Chem. Commun. 2000, 669-670.
    • (2000) Chem. Commun , pp. 669-670
    • Manabe, K.1    Kobayashi, S.2
  • 18
    • 0346732034 scopus 로고    scopus 로고
    • One-pot synthesis of α-amino phosphonates using samarium diiodide as a catalyst precursor
    • Xu, F.; Luo, Y.; Deng, M.; Shen, Q. One-pot synthesis of α-amino phosphonates using samarium diiodide as a catalyst precursor. Eur. J. Org. Chem. 2003, 4728-4730.
    • (2003) Eur. J. Org. Chem , pp. 4728-4730
    • Xu, F.1    Luo, Y.2    Deng, M.3    Shen, Q.4
  • 20
    • 0043210612 scopus 로고    scopus 로고
    • Synthesis of tertiary α-amino phosphonate by one-pot three-component coupling mediated by LPDE
    • Azizi, N.; Saidi, M. R. Synthesis of tertiary α-amino phosphonate by one-pot three-component coupling mediated by LPDE. Tetrahedron 2003, 59, 5329-5332.
    • (2003) Tetrahedron , vol.59 , pp. 5329-5332
    • Azizi, N.1    Saidi, M.R.2
  • 21
    • 0034941662 scopus 로고    scopus 로고
    • Montmorillonite clay-catalyzed one-pot synthesis of a-amino phosphonates
    • (a) Yadav, J. S.; Reddy, B. V. S.; Madan, C. Montmorillonite clay-catalyzed one-pot synthesis of a-amino phosphonates. Synlett 2001, 1131-1133;
    • (2001) Synlett , pp. 1131-1133
    • Yadav, J.S.1    Reddy, B.V.S.2    Madan, C.3
  • 22
    • 0035851395 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions
    • (b) Kaboudin, B.; Nazari, R. Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions. Tetrahedron Lett. 2001, 42, 8211-8213;
    • (2001) Tetrahedron Lett , vol.42 , pp. 8211-8213
    • Kaboudin, B.1    Nazari, R.2
  • 23
    • 26044457336 scopus 로고    scopus 로고
    • Microwave-assisted one-pot synthesis of α-amino phosphonates via three component coupling on a silica gel support
    • (c) Zhan, Z. P.; Yang, R. F.; Li, J. P. Microwave-assisted one-pot synthesis of α-amino phosphonates via three component coupling on a silica gel support. Chem. Lett. 2005, 34, 1042-1043.
    • (2005) Chem. Lett , vol.34 , pp. 1042-1043
    • Zhan, Z.P.1    Yang, R.F.2    Li, J.P.3
  • 24
    • 21844520646 scopus 로고
    • Synthese von fluorierten N- arylaminoarylmethan-phosphonsauredialkylestern
    • Gruss, U.; Haegele, G. Synthese von fluorierten N- arylaminoarylmethan-phosphonsauredialkylestern. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 97, 209-221.
    • (1994) Phosphorus, Sulfur Silicon Relat. Elem , vol.97 , pp. 209-221
    • Gruss, U.1    Haegele, G.2
  • 26
    • 0009333041 scopus 로고
    • Synthesis of perfluoroalkanesulfonylaminoalkylphosphonic acids
    • Zhu, S. Z.; Jin, X. L. Synthesis of perfluoroalkanesulfonylaminoalkylphosphonic acids. J. Fluorine Chem. 1995, 72, 19-22.
    • (1995) J. Fluorine Chem , vol.72 , pp. 19-22
    • Zhu, S.Z.1    Jin, X.L.2
  • 27
    • 3042577362 scopus 로고    scopus 로고
    • Microwave-promoted solvent-free one-pot three-component reaction to 2-pentafluorophenylquinoline derivatives
    • Zhang, J. M.; Yang, W.; Song, L. P.; Cai, X.; Zhu, S. Z. Microwave-promoted solvent-free one-pot three-component reaction to 2-pentafluorophenylquinoline derivatives. Tetrahedron Lett. 2004, 45, 5771-5773.
    • (2004) Tetrahedron Lett , vol.45 , pp. 5771-5773
    • Zhang, J.M.1    Yang, W.2    Song, L.P.3    Cai, X.4    Zhu, S.Z.5
  • 28
    • 2442655249 scopus 로고    scopus 로고
    • CAN catalyzed one-pot synthesis of α-amino phosphonates from carbonyl compounds
    • Ravinder, K.; Reddy, A. V.; Krishnaiah, P.; Venkataramana, G.; Niranjan, R. V. L. CAN catalyzed one-pot synthesis of α-amino phosphonates from carbonyl compounds. Synth. Comm. 2004, 34, 1677-1683.
    • (2004) Synth. Comm , vol.34 , pp. 1677-1683
    • Ravinder, K.1    Reddy, A.V.2    Krishnaiah, P.3    Venkataramana, G.4    Niranjan, R.V.L.5
  • 29
    • 0000555734 scopus 로고    scopus 로고
    • Mastryukova, T. A.; Aladzheva, I. M.; Leont'eva, I. V.; Petrovski, P. V.; Fedin, E. I.; Kabachnik, M. I. Dyadic. phosphorus-carbon tautomerism. Pure Appl. Chem. 1980, 52, 945-957, and references therein.
    • Mastryukova, T. A.; Aladzheva, I. M.; Leont'eva, I. V.; Petrovski, P. V.; Fedin, E. I.; Kabachnik, M. I. Dyadic. phosphorus-carbon tautomerism. Pure Appl. Chem. 1980, 52, 945-957, and references therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.