메뉴 건너뛰기




Volumn 40, Issue 1, 2003, Pages 113-120

N-phenyl-substituted pyrrolidines, piperidines and azabicyclics by a tandem reduction-double reductive amination reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANILINE; AROMATIC NITRO COMPOUND; BICYCLO COMPOUND; CARBONYL DERIVATIVE; CYCLOALKANONE; ESTER; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; HYDROXYLAMINE; NITROBENZENE; PHENYL GROUP; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

EID: 0037287587     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570400115     Document Type: Article
Times cited : (9)

References (44)
  • 1
    • 85006873467 scopus 로고    scopus 로고
    • Undergraduate research participants: D. H. M. 1999-present; J. R. L. 2001-2002
    • Undergraduate research participants: D. H. M. 1999-present; J. R. L. 2001-2002.
  • 7
    • 0017387939 scopus 로고
    • Cyclization by reductive amination using amines and ammonium salts: [a] R. F. Borch and B. C. Ho, J. Org. Chem., 42, 1225 (1977). [b] T. H. Jones, J. B. Franko, M. S. Blum and H. M. Fales, Tetrahedron Lett., 21, 789 (1980). [c] T. H. Jones, M. S. Blum, H. M. Fales and C. R. Thompson, J. Org. Chem., 45, 4778 (1980). [d] M. Kawaguchi, J. Ohashi, Y. Kawakami, Y. Yamamoto and J. Oda, Synthesis, 701 (1985). [e] A. H. Fray, D. J. Augeri and E. F. Kleinman, J. Org. Chem., 53, 896 (1988). [f] C. Boga, F. Manescalchi and D. Savoia, Tetrahedron, 50, 4709 (1994). [g] T. T. Shawe, C. J. Sheils, S. M. Gray and J. L. Conard, J. Org. Chem., 59, 5841 (1994).
    • (1977) J. Org. Chem. , vol.42 , pp. 1225
    • Borch, R.F.1    Ho, B.C.2
  • 8
    • 0001733280 scopus 로고
    • Cyclization by reductive amination using amines and ammonium salts: [a] R. F. Borch and B. C. Ho, J. Org. Chem., 42, 1225 (1977). [b] T. H. Jones, J. B. Franko, M. S. Blum and H. M. Fales, Tetrahedron Lett., 21, 789 (1980). [c] T. H. Jones, M. S. Blum, H. M. Fales and C. R. Thompson, J. Org. Chem., 45, 4778 (1980). [d] M. Kawaguchi, J. Ohashi, Y. Kawakami, Y. Yamamoto and J. Oda, Synthesis, 701 (1985). [e] A. H. Fray, D. J. Augeri and E. F. Kleinman, J. Org. Chem., 53, 896 (1988). [f] C. Boga, F. Manescalchi and D. Savoia, Tetrahedron, 50, 4709 (1994). [g] T. T. Shawe, C. J. Sheils, S. M. Gray and J. L. Conard, J. Org. Chem., 59, 5841 (1994).
    • (1980) Tetrahedron Lett. , vol.21 , pp. 789
    • Jones, T.H.1    Franko, J.B.2    Blum, M.S.3    Fales, H.M.4
  • 9
    • 0000882942 scopus 로고
    • Cyclization by reductive amination using amines and ammonium salts: [a] R. F. Borch and B. C. Ho, J. Org. Chem., 42, 1225 (1977). [b] T. H. Jones, J. B. Franko, M. S. Blum and H. M. Fales, Tetrahedron Lett., 21, 789 (1980). [c] T. H. Jones, M. S. Blum, H. M. Fales and C. R. Thompson, J. Org. Chem., 45, 4778 (1980). [d] M. Kawaguchi, J. Ohashi, Y. Kawakami, Y. Yamamoto and J. Oda, Synthesis, 701 (1985). [e] A. H. Fray, D. J. Augeri and E. F. Kleinman, J. Org. Chem., 53, 896 (1988). [f] C. Boga, F. Manescalchi and D. Savoia, Tetrahedron, 50, 4709 (1994). [g] T. T. Shawe, C. J. Sheils, S. M. Gray and J. L. Conard, J. Org. Chem., 59, 5841 (1994).
    • (1980) J. Org. Chem. , vol.45 , pp. 4778
    • Jones, T.H.1    Blum, M.S.2    Fales, H.M.3    Thompson, C.R.4
  • 10
    • 1942497466 scopus 로고
    • Cyclization by reductive amination using amines and ammonium salts: [a] R. F. Borch and B. C. Ho, J. Org. Chem., 42, 1225 (1977). [b] T. H. Jones, J. B. Franko, M. S. Blum and H. M. Fales, Tetrahedron Lett., 21, 789 (1980). [c] T. H. Jones, M. S. Blum, H. M. Fales and C. R. Thompson, J. Org. Chem., 45, 4778 (1980). [d] M. Kawaguchi, J. Ohashi, Y. Kawakami, Y. Yamamoto and J. Oda, Synthesis, 701 (1985). [e] A. H. Fray, D. J. Augeri and E. F. Kleinman, J. Org. Chem., 53, 896 (1988). [f] C. Boga, F. Manescalchi and D. Savoia, Tetrahedron, 50, 4709 (1994). [g] T. T. Shawe, C. J. Sheils, S. M. Gray and J. L. Conard, J. Org. Chem., 59, 5841 (1994).
    • (1985) Synthesis , pp. 701
    • Kawaguchi, M.1    Ohashi, J.2    Kawakami, Y.3    Yamamoto, Y.4    Oda, J.5
  • 11
    • 0023831585 scopus 로고
    • Cyclization by reductive amination using amines and ammonium salts: [a] R. F. Borch and B. C. Ho, J. Org. Chem., 42, 1225 (1977). [b] T. H. Jones, J. B. Franko, M. S. Blum and H. M. Fales, Tetrahedron Lett., 21, 789 (1980). [c] T. H. Jones, M. S. Blum, H. M. Fales and C. R. Thompson, J. Org. Chem., 45, 4778 (1980). [d] M. Kawaguchi, J. Ohashi, Y. Kawakami, Y. Yamamoto and J. Oda, Synthesis, 701 (1985). [e] A. H. Fray, D. J. Augeri and E. F. Kleinman, J. Org. Chem., 53, 896 (1988). [f] C. Boga, F. Manescalchi and D. Savoia, Tetrahedron, 50, 4709 (1994). [g] T. T. Shawe, C. J. Sheils, S. M. Gray and J. L. Conard, J. Org. Chem., 59, 5841 (1994).
    • (1988) J. Org. Chem. , vol.53 , pp. 896
    • Fray, A.H.1    Augeri, D.J.2    Kleinman, E.F.3
  • 12
    • 0028298596 scopus 로고
    • Cyclization by reductive amination using amines and ammonium salts: [a] R. F. Borch and B. C. Ho, J. Org. Chem., 42, 1225 (1977). [b] T. H. Jones, J. B. Franko, M. S. Blum and H. M. Fales, Tetrahedron Lett., 21, 789 (1980). [c] T. H. Jones, M. S. Blum, H. M. Fales and C. R. Thompson, J. Org. Chem., 45, 4778 (1980). [d] M. Kawaguchi, J. Ohashi, Y. Kawakami, Y. Yamamoto and J. Oda, Synthesis, 701 (1985). [e] A. H. Fray, D. J. Augeri and E. F. Kleinman, J. Org. Chem., 53, 896 (1988). [f] C. Boga, F. Manescalchi and D. Savoia, Tetrahedron, 50, 4709 (1994). [g] T. T. Shawe, C. J. Sheils, S. M. Gray and J. L. Conard, J. Org. Chem., 59, 5841 (1994).
    • (1994) Tetrahedron , vol.50 , pp. 4709
    • Boga, C.1    Manescalchi, F.2    Savoia, D.3
  • 13
    • 0028088777 scopus 로고
    • Cyclization by reductive amination using amines and ammonium salts: [a] R. F. Borch and B. C. Ho, J. Org. Chem., 42, 1225 (1977). [b] T. H. Jones, J. B. Franko, M. S. Blum and H. M. Fales, Tetrahedron Lett., 21, 789 (1980). [c] T. H. Jones, M. S. Blum, H. M. Fales and C. R. Thompson, J. Org. Chem., 45, 4778 (1980). [d] M. Kawaguchi, J. Ohashi, Y. Kawakami, Y. Yamamoto and J. Oda, Synthesis, 701 (1985). [e] A. H. Fray, D. J. Augeri and E. F. Kleinman, J. Org. Chem., 53, 896 (1988). [f] C. Boga, F. Manescalchi and D. Savoia, Tetrahedron, 50, 4709 (1994). [g] T. T. Shawe, C. J. Sheils, S. M. Gray and J. L. Conard, J. Org. Chem., 59, 5841 (1994).
    • (1994) J. Org. Chem. , vol.59 , pp. 5841
    • Shawe, T.T.1    Sheils, C.J.2    Gray, S.M.3    Conard, J.L.4
  • 16
    • 0004198491 scopus 로고
    • Wiley-Interscience, New York, NY
    • For several general reviews on tandem reactions, see [a] T.-L. Ho, Tandem Organic Reactions, Wiley-Interscience, New York, NY, 1992. [b] L. F. Tietze and U. Beifuss, Angew. Chem. Int. Ed. Eng., 32, 131 (1993). [c] R. A. Bunce, Tetrahedron, 51, 13103 (1995).
    • (1992) Tandem Organic Reactions
    • Ho, T.-L.1
  • 17
    • 33750173220 scopus 로고
    • For several general reviews on tandem reactions, see [a] T.-L. Ho, Tandem Organic Reactions, Wiley-Interscience, New York, NY, 1992. [b] L. F. Tietze and U. Beifuss, Angew. Chem. Int. Ed. Eng., 32, 131 (1993). [c] R. A. Bunce, Tetrahedron, 51, 13103 (1995).
    • (1993) Angew. Chem. Int. Ed. Eng. , vol.32 , pp. 131
    • Tietze, L.F.1    Beifuss, U.2
  • 18
    • 0028879573 scopus 로고
    • For several general reviews on tandem reactions, see [a] T.-L. Ho, Tandem Organic Reactions, Wiley-Interscience, New York, NY, 1992. [b] L. F. Tietze and U. Beifuss, Angew. Chem. Int. Ed. Eng., 32, 131 (1993). [c] R. A. Bunce, Tetrahedron, 51, 13103 (1995).
    • (1995) Tetrahedron , vol.51 , pp. 13103
    • Bunce, R.A.1
  • 21
    • 0042670967 scopus 로고
    • Wiley, New York, NY
    • [c] For a preparation of N, N-dimethylhydrazones, see G. R. Newkome and D. L. Fishel, Organic. Syntheses, Coll. Vol. VI, Wiley, New York, NY, 1988, p 12-13.
    • (1988) Organic. Syntheses, Coll. , vol.7 , pp. 12-13
    • Newkome, G.R.1    Fishel, D.L.2
  • 26
    • 85006874621 scopus 로고    scopus 로고
    • See ref 2, p 12
    • [b] See ref 2, p 12.
  • 33
    • 85006883507 scopus 로고    scopus 로고
    • See ref. 2, p 152
    • [b] See ref. 2, p 152.
  • 34
    • 85006853643 scopus 로고    scopus 로고
    • note
    • [c] The exact percentage of each compound varied with reaction time - longer reaction times resulted in more of the fully deoxygenated product.
  • 35
    • 85006931288 scopus 로고    scopus 로고
    • note
    • [d] Since a large amount of the benzylic alcohol was isolated in these reactions, it was assumed that the deoxygenated product was produced in two stages from the phenyl ketone. A referee, however, pointed out that the fully deoxygenated product could also arise from hydrogenolysis of the benzylic amine in the ring-closed product. A control experiment using 1,2-diphenylpyrrolidine under typical reaction conditions gave some decomposition, but none of the N-(4-phenylbutyl)benzenamine.
  • 38
    • 0001673915 scopus 로고
    • W. S. Emerson and C. A. Uraneck, J. Am. Chem. Soc., 63, 749 (1941). These reactions were run in ethanol-acetic acid using platinum(IV) oxide as the catalyst.
    • (1941) J. Am. Chem. Soc. , vol.63 , pp. 749
    • Emerson, W.S.1    Uraneck, C.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.