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Volumn , Issue 6, 1998, Pages 1219-1226

A study of vinyl radical cyclization onto the azido group by addition of sulfanyl, stannyl, and silyl radicals to alkynyl azides

Author keywords

Alkynes; Azides; Cyclizations; Indoles; Radicals

Indexed keywords


EID: 0001882726     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199806)1998:6<1219::AID-EJOC1219>3.0.CO;2-V     Document Type: Article
Times cited : (57)

References (54)
  • 2
    • 0000315424 scopus 로고
    • Radical Cyclizations and Sequential Radical Reactions
    • Pergamon Press, Oxford, U.K., Chapter 4.2
    • D. P. Curran, "Radical Cyclizations and Sequential Radical Reactions" in Comprehensive Organic Synthesis, Pergamon Press, Oxford, U.K., 1991, vol. 4, Chapter 4.2.
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Curran, D.P.1
  • 12
    • 0028348460 scopus 로고
    • S. Atmaran, A. E. Forrester, M. Gill, R. H. Thomson, J. Chem. Soc , Perkin Trans 1 1981, 1721-1724; J. Biovin, E. Fouquet, S. Z. Zard, Tetrahedron 1994, 50, 1745-1756; L. E. Kaim, C. Meyer, J. Org. Chem. 1996, 61, 1556-1557.
    • (1994) Tetrahedron , vol.50 , pp. 1745-1756
    • Biovin, J.1    Fouquet, E.2    Zard, S.Z.3
  • 13
    • 0000107516 scopus 로고    scopus 로고
    • S. Atmaran, A. E. Forrester, M. Gill, R. H. Thomson, J. Chem. Soc , Perkin Trans 1 1981, 1721-1724; J. Biovin, E. Fouquet, S. Z. Zard, Tetrahedron 1994, 50, 1745-1756; L. E. Kaim, C. Meyer, J. Org. Chem. 1996, 61, 1556-1557.
    • (1996) J. Org. Chem. , vol.61 , pp. 1556-1557
    • Kaim, L.E.1    Meyer, C.2
  • 14
    • 0029026578 scopus 로고
    • W. R. Bowmann, P. T. Stephenson, N. K. Terrett, A. R. Young, Tetrahedron 1995, 51, 7959-7980; M. J. Tomaszewski, J. Warkentin, N. H. Werstiuk, Aust. J. Chem. 1995, 48, 291-321; S. Takano, M. Suzuki, K. Ogasawara, Heterocycles 1994, 37, 149-153; M. Gioanola, R. Leardini, D. Nanni, P. Parcschi, G. Zanardi, Tetrahedron 1995, 51, 2039-2054.
    • (1995) Tetrahedron , vol.51 , pp. 7959-7980
    • Bowmann, W.R.1    Stephenson, P.T.2    Terrett, N.K.3    Young, A.R.4
  • 15
    • 84970557675 scopus 로고
    • W. R. Bowmann, P. T. Stephenson, N. K. Terrett, A. R. Young, Tetrahedron 1995, 51, 7959-7980; M. J. Tomaszewski, J. Warkentin, N. H. Werstiuk, Aust. J. Chem. 1995, 48, 291-321; S. Takano, M. Suzuki, K. Ogasawara, Heterocycles 1994, 37, 149-153; M. Gioanola, R. Leardini, D. Nanni, P. Parcschi, G. Zanardi, Tetrahedron 1995, 51, 2039-2054.
    • (1995) Aust. J. Chem. , vol.48 , pp. 291-321
    • Tomaszewski, M.J.1    Warkentin, J.2    Werstiuk, N.H.3
  • 16
    • 0000231304 scopus 로고
    • W. R. Bowmann, P. T. Stephenson, N. K. Terrett, A. R. Young, Tetrahedron 1995, 51, 7959-7980; M. J. Tomaszewski, J. Warkentin, N. H. Werstiuk, Aust. J. Chem. 1995, 48, 291-321; S. Takano, M. Suzuki, K. Ogasawara, Heterocycles 1994, 37, 149-153; M. Gioanola, R. Leardini, D. Nanni, P. Parcschi, G. Zanardi, Tetrahedron 1995, 51, 2039-2054.
    • (1994) Heterocycles , vol.37 , pp. 149-153
    • Takano, S.1    Suzuki, M.2    Ogasawara, K.3
  • 17
    • 0028896022 scopus 로고
    • W. R. Bowmann, P. T. Stephenson, N. K. Terrett, A. R. Young, Tetrahedron 1995, 51, 7959-7980; M. J. Tomaszewski, J. Warkentin, N. H. Werstiuk, Aust. J. Chem. 1995, 48, 291-321; S. Takano, M. Suzuki, K. Ogasawara, Heterocycles 1994, 37, 149-153; M. Gioanola, R. Leardini, D. Nanni, P. Parcschi, G. Zanardi, Tetrahedron 1995, 51, 2039-2054.
    • (1995) Tetrahedron , vol.51 , pp. 2039-2054
    • Gioanola, M.1    Leardini, R.2    Nanni, D.3    Parcschi, P.4    Zanardi, G.5
  • 21
    • 0000722245 scopus 로고
    • S. Kim, G. H. Joe, J. Y. Do, J. Am. Chem. Soc 1994, 116, 5521-5522; M. Kizil, J. A. Murphy, J. Chem. Soc., Chem. Commun. 1995, 1409-1410.
    • (1994) J. Am. Chem. Soc , vol.116 , pp. 5521-5522
    • Kim, S.1    Joe, G.H.2    Do, J.Y.3
  • 31
    • 0030919829 scopus 로고    scopus 로고
    • L. Benati, G. Calestani, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron 1997, 53, 9269-9278; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, P. Zanirato, J. Chem. Soc., Perkin Trans. 1 1996, 2561-2563; A. Capperucci, A. Degl'innocenti, M. Funicello, G. Mauriello, P. Scafato, P. Spagnolo, J. Org. Chem. 1995, 60, 2254-2256; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, Chem. Leu. 1994, 1873-1876; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231-243.
    • (1997) Tetrahedron , vol.53 , pp. 9269-9278
    • Benati, L.1    Calestani, G.2    Nanni, D.3    Spagnolo, P.4    Volta, M.5
  • 32
    • 33748977106 scopus 로고    scopus 로고
    • L. Benati, G. Calestani, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron 1997, 53, 9269-9278; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, P. Zanirato, J. Chem. Soc., Perkin Trans. 1 1996, 2561-2563; A. Capperucci, A. Degl'innocenti, M. Funicello, G. Mauriello, P. Scafato, P. Spagnolo, J. Org. Chem. 1995, 60, 2254-2256; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, Chem. Leu. 1994, 1873-1876; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231-243.
    • (1996) J. Chem. Soc., Perkin Trans. 1 , pp. 2561-2563
    • Degl'innocenti, A.1    Funicello, M.2    Scafato, P.3    Spagnolo, P.4    Zanirato, P.5
  • 33
    • 0000801310 scopus 로고
    • L. Benati, G. Calestani, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron 1997, 53, 9269-9278; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, P. Zanirato, J. Chem. Soc., Perkin Trans. 1 1996, 2561-2563; A. Capperucci, A. Degl'innocenti, M. Funicello, G. Mauriello, P. Scafato, P. Spagnolo, J. Org. Chem. 1995, 60, 2254-2256; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, Chem. Leu. 1994, 1873-1876; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231-243.
    • (1995) J. Org. Chem. , vol.60 , pp. 2254-2256
    • Capperucci, A.1    Degl'innocenti, A.2    Funicello, M.3    Mauriello, G.4    Scafato, P.5    Spagnolo, P.6
  • 34
    • 0039240292 scopus 로고
    • L. Benati, G. Calestani, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron 1997, 53, 9269-9278; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, P. Zanirato, J. Chem. Soc., Perkin Trans. 1 1996, 2561-2563; A. Capperucci, A. Degl'innocenti, M. Funicello, G. Mauriello, P. Scafato, P. Spagnolo, J. Org. Chem. 1995, 60, 2254-2256; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, Chem. Leu. 1994, 1873-1876; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231-243.
    • (1994) Chem. Leu. , pp. 1873-1876
    • Degl'innocenti, A.1    Funicello, M.2    Scafato, P.3    Spagnolo, P.4
  • 35
    • 0039240285 scopus 로고
    • L. Benati, G. Calestani, D. Nanni, P. Spagnolo, M. Volta, Tetrahedron 1997, 53, 9269-9278; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, P. Zanirato, J. Chem. Soc., Perkin Trans. 1 1996, 2561-2563; A. Capperucci, A. Degl'innocenti, M. Funicello, G. Mauriello, P. Scafato, P. Spagnolo, J. Org. Chem. 1995, 60, 2254-2256; A. Degl'innocenti, M. Funicello, P. Scafato, P. Spagnolo, Chem. Leu. 1994, 1873-1876; M. Funicello, P. Spagnolo, P. Zanirato, Acta Chem. Scand. 1993, 47, 231-243.
    • (1993) Acta Chem. Scand. , vol.47 , pp. 231-243
    • Funicello, M.1    Spagnolo, P.2    Zanirato, P.3
  • 37
    • 0000923540 scopus 로고
    • For previous reports on thiol-mediated radical cyclizations of alkynes see refs.(([9b][9c][9g][9h])). See also: C. A. Broka, D. E. C. Reichert, Tetrahedron Lett. 1987, 28, 1503-1506 and L. El Kaim, A. Gacon, A. Perroux, Tetrahedron Lett. 1998, 39, 371-374.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 1503-1506
    • Broka, C.A.1    Reichert, D.E.C.2
  • 38
    • 0032576814 scopus 로고    scopus 로고
    • For previous reports on thiol-mediated radical cyclizations of alkynes see refs.(([9b][9c][9g][9h])). See also: C. A. Broka, D. E. C. Reichert, Tetrahedron Lett. 1987, 28, 1503-1506 and L. El Kaim, A. Gacon, A. Perroux, Tetrahedron Lett. 1998, 39, 371-374.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 371-374
    • El Kaim, L.1    Gacon, A.2    Perroux, A.3
  • 39
    • 0343174026 scopus 로고
    • Radical Addition Involving CC Triple Bonds
    • Ed.: S. Patai, J. Wiley, New York, Chapter 16
    • [13a]C. Chatgilialoglu, C. Ferreri, "Radical Addition Involving CC Triple Bonds" in The Chemistry of Triple-Bonded Functional Groups (Ed.: S. Patai), J. Wiley, New York, 1994, Suppl. C2, Vol. 2, Chapter 16.
    • (1994) The Chemistry of Triple-Bonded Functional Groups , vol.2 , Issue.2 SUPPL. C
    • Chatgilialoglu, C.1    Ferreri, C.2
  • 40
    • 0001216647 scopus 로고
    • Radical Addition Reactions
    • Pergamon Press, Oxford, U.K., Chapter 4.1
    • [13b]D. P. Curran, "Radical Addition Reactions" in Comprehensive Organic Synthesis, Pergamon Press, Oxford, U.K., 1991, Vol. 4, Chapter 4.1.
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Curran, D.P.1
  • 44
    • 2742593510 scopus 로고    scopus 로고
    • note
    • Arenethiols are more powerful hydrogen donors than alkanethiols as a result of their lower S-H bond strength (80 and 88 kcal/mol, respectively). The syringe pump technique allowed the use of a very low concentration of benzenethiol 1c.
  • 46
    • 0001080034 scopus 로고
    • [10g]; see also: O. Ito, R. Omori, M. Matsuda, J Am. Chem. Soc. 1982, 104, 3934-3937, and S. W. Benson, Chem. Rev. 1978, 78, 23-35.
    • (1982) J Am. Chem. Soc. , vol.104 , pp. 3934-3937
    • Ito, O.1    Omori, R.2    Matsuda, M.3
  • 47
    • 0002226173 scopus 로고
    • [10g]; see also: O. Ito, R. Omori, M. Matsuda, J Am. Chem. Soc. 1982, 104, 3934-3937, and S. W. Benson, Chem. Rev. 1978, 78, 23-35.
    • (1978) Chem. Rev. , vol.78 , pp. 23-35
    • Benson, S.W.1
  • 49
    • 0001561381 scopus 로고
    • 3SnH or TMSS even though sulfur-hydrogen bonds in the alkanethiols are relatively strong (see: M. Newcomb, A. G. Glenn, M. B. Maneck, J. Org. Chem. 1989, 54, 4603-4606; C. Chatigilialoglu, Acc. Chem. Res. 1992, 25, 188-194; M. Ballestri, C. Chatgilialoglu, P. Dembech, A. Guerrini, G. Seconi in Sulfur-Centered Reactive Intermediates in Chemistry and Biology (Eds.: C. Chatgilialoglu, K.-D. Asmus), Plenum Press, New York, 1990, pp. 319-325.
    • (1989) J. Org. Chem. , vol.54 , pp. 4603-4606
    • Newcomb, M.1    Glenn, A.G.2    Maneck, M.B.3
  • 50
    • 0000829322 scopus 로고
    • 3SnH or TMSS even though sulfur-hydrogen bonds in the alkanethiols are relatively strong (see: M. Newcomb, A. G. Glenn, M. B. Maneck, J. Org. Chem. 1989, 54, 4603-4606; C. Chatigilialoglu, Acc. Chem. Res. 1992, 25, 188-194; M. Ballestri, C. Chatgilialoglu, P. Dembech, A. Guerrini, G. Seconi in Sulfur-Centered Reactive Intermediates in Chemistry and Biology (Eds.: C. Chatgilialoglu, K.-D. Asmus), Plenum Press, New York, 1990, pp. 319-325.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 188-194
    • Chatigilialoglu, C.1
  • 51
    • 2742522164 scopus 로고
    • Eds.: C. Chatgilialoglu, K.-D. Asmus, Plenum Press, New York
    • 3SnH or TMSS even though sulfur-hydrogen bonds in the alkanethiols are relatively strong (see: M. Newcomb, A. G. Glenn, M. B. Maneck, J. Org. Chem. 1989, 54, 4603-4606; C. Chatigilialoglu, Acc. Chem. Res. 1992, 25, 188-194; M. Ballestri, C. Chatgilialoglu, P. Dembech, A. Guerrini, G. Seconi in Sulfur-Centered Reactive Intermediates in Chemistry and Biology (Eds.: C. Chatgilialoglu, K.-D. Asmus), Plenum Press, New York, 1990, pp. 319-325.
    • (1990) Sulfur-Centered Reactive Intermediates in Chemistry and Biology , pp. 319-325
    • Ballestri, M.1    Chatgilialoglu, C.2    Dembech, P.3    Guerrini, A.4    Seconi, G.5


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