메뉴 건너뛰기




Volumn , Issue 1, 1999, Pages 59-69

Intramolecular cycloadditions with 1-aminoisobenzofurans: A simple entry into the field of polycyclic aza-compounds

Author keywords

[No Author keywords available]

Indexed keywords


EID: 33746573760     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806916f     Document Type: Article
Times cited : (18)

References (196)
  • 14
    • 33746525736 scopus 로고
    • Angew. Chem., Int. Ed Engl., 1988, 27, 568
    • (a) W. berbach, H. Fritz and N. Labert, Angeu: Chem., 1988, 100, 599; Angew. Chem., Int. Ed Engl., 1988, 27, 568;
    • (1988) Angeu: Chem. , vol.100
    • Berbach, W.1    Fritz, H.2    Labert, N.3
  • 30
    • 33746502232 scopus 로고    scopus 로고
    • 6
    • The literature of intramolecular Diels-Alder reactions is extensive. For reviews and examples see réf. 6.
  • 31
    • 33746553050 scopus 로고
    • Angcn: Chcm., Int. Eel. Engt, 1977, 16, 10
    • (a) W. Oppolzer, Angeu: Clicm., 1977,89, 10; Angcn: Chcm., Int. Eel. Engt, 1977, 16, 10;
    • (1977) Angeu: Clicm. , vol.89
    • Oppolzer, W.1
  • 60
    • 33746523179 scopus 로고
    • (ee) W. R. Roush, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 5, p. 513. For the phrase "tandem" see also L. F. Tietze, Chem. Rev., 1996,36, 115, and footnote.
    • dd) D. Craig, in Houbcn-IVcyl, Methods of Organic Synthesis, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme Verlag, Stuttgart, 1995, vol. E21c, p. 2872; (ee) W. R. Roush, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 5, p. 513. For the phrase "tandem" see also L. F. Tietze, Chem. Rev., 1996,36, 115, and footnote.
    • (1995) Houbcn-IVcyl, Methods of Organic Synthesis, Ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Thieme Verlag, Stuttgart , vol.21
    • Craig, D.1
  • 61
    • 33746501664 scopus 로고    scopus 로고
    • 3and8
    • Benzo[c]furans have been used as synthons for the preparation of a wide variety of products. For pertinent examples see refs. 3 and 8-
  • 85
    • 0030018220 scopus 로고    scopus 로고
    • see also: A. Padwa, C. O. Kappe and T. S. Reger, 76' International Congress on Ileterocyclic Chemistry, Montana State University, Bozeman, August 10-15, 1997, Abstr. Paper OP-I1.
    • An ingenious route towards erythrinanes using aminoisobenzofuranes as intermediates was reported by A. Padwa and co-workers: A. Padwa, C. O. Kappe and T. S. Reger, J. Org. Chem., 1996, 61, 4888; see also: A. Padwa, C. O. Kappe and T. S. Reger, 76' International Congress on Ileterocyclic Chemistry, Montana State University, Bozeman, August 10-15, 1997, Abstr. Paper OP-I1.
    • (1996) J. Org. Chem. , vol.61
    • Padwa, A.1    Kappe, C.O.2    Reger, T.S.3
  • 91
    • 33746540759 scopus 로고
    • 279 for an wiregioselectire ring opening reaction of homophthalic anhydride.
    • For a similar reaction in the furan series see: R. W. Carling and P. D. Leeson, Synlett, 1993, 40; but see also W. V. Murray and S. K. Hadden, J. Client. Res., 1991, 279 for an wiregioselectire ring opening reaction of homophthalic anhydride.
    • (1993) Synlett , vol.40
    • Carling, R.W.1    Leeson, P.D.2
  • 92
    • 33746510264 scopus 로고
    • A convenient synthesis of 1 starting with -anisic acid has been worked out by K. Hildebrandt: K. Hildebrandt, Diploma thesis, University of Kiel, Germany, 1985.
    • (1985)
  • 96
    • 33746494720 scopus 로고    scopus 로고
    • 5-bromopent-I-ene with aqueous methylamine (40%, 1 h, 80 °C) is more convenient than the method described by von Braun and Köhler."
    • Treatment of 5-bromopent-I-ene with aqueous methylamine (40%, 1 h, 80 °C) is more convenient than the method described by von Braun and Köhler."
  • 97
    • 33746476084 scopus 로고
    • Dissertation, University of Kiel, Germany
    • A. Schönina, Dissertation, University of Kiel, Germany, 1989.
    • (1989)
  • 102
    • 33746558319 scopus 로고
    • M. Schildberg, Dissertation, University of Kiel, Germany
    • M. Schildberg, Dissertation, University of Kiel, Germany, 1987;
    • (1987)
  • 106
    • 33746487674 scopus 로고
    • A primary cycloadduct of similar type could be isolated when the quantity of transition metal catalyst was reduced to only a minimal amount: K. Hildebrandt, Dissertation, University of Kiel, Germany
    • A primary cycloadduct of similar type could be isolated when the quantity of transition metal catalyst was reduced to only a minimal amount: K. Hildebrandt, Dissertation, University of Kiel, Germany, 1988.
    • (1988)
  • 107
    • 33746551345 scopus 로고    scopus 로고
    • For more details consult the Fachinformationszentrum Karlsruhe, 7634
    • For more details consult the Fachinformationszentrum Karlsruhe, 76344 Eggenstein-Leopoldshafen under number CSD-404892.
    • , vol.4
  • 111
    • 33746489686 scopus 로고
    • J. Gen. Chcm. USSR (Engl. Transi.), 1971, 41, 242
    • Y. P. Badanova and K. K. Pivnitskii, Zh. Obshch. Khim, 1971, 41, 242; J. Gen. Chcm. USSR (Engl. Transi.), 1971, 41, 242;
    • (1971) Zh. Obshch. Khim , vol.41
    • Badanova, Y.P.1    Pivnitskii, K.K.2
  • 112
    • 0031214263 scopus 로고    scopus 로고
    • and references cited therein.
    • J. R. Hanson, Nat. Prod. Rep., 1997,14, 373 and references cited therein.
    • (1997) Nat. Prod. Rep. , vol.14
    • Hanson, J.R.1
  • 119
    • 33746531383 scopus 로고
    • B.-M. König, Dissertation, University of Kiel, Germany
    • B.-M. König, Dissertation, University of Kiel, Germany, 1987.
    • (1987)
  • 129
    • 33746576560 scopus 로고    scopus 로고
    • 37 MOPAC, Ver. 6.0 and Ver. 6.12 were used.38
    • 37 MOPAC, Ver. 6.0 and Ver. 6.12 were used.38
  • 130
    • 33746527749 scopus 로고
    • 72
    • QCMP 113, QCPEBidi, 1992,12, 72.
    • (1992) QCPEBidi , vol.12
  • 137
    • 33746515298 scopus 로고    scopus 로고
    • Gaussian 92, Revision E.2, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, J. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart and J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1992; Gaussian 92/DFT, Revision G. 3, M. J. Frisch, G. \V~Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. W. Wong, J. B. Foresman, Ivf. A. Robb, M. HeadGordon, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, J. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart and J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1993
    • (a) Gaussian 92, Revision E.2, M. J. Frisch, G. W. Trucks, M. Head-Gordon, P. M. W. Gill, M. W. Wong, J. B. Foresman, B. G. Johnson, H. B. Schlegel, M. A. Robb, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, J. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart and J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1992; Gaussian 92/DFT, Revision G. 3, M. J. Frisch, G. \V~Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. W. Wong, J. B. Foresman, Ivf. A. Robb, M. HeadGordon, E. S. Replogle, R. Gomperts, J. L. Andres, K. Raghavachari, J. S. Binkley, C. Gonzalez, R. L. Martin, J. J. Fox, D. J. Defrees, J. Baker, J. J. P. Stewart and J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1993;
  • 138
    • 33746555732 scopus 로고
    • Gaussian 94, Revision D.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wonc, J. L'.-Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, Gaussian Inc., Pittsburgh PA
    • (b) Gaussian 94, Revision D.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wonc, J. L'.-Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, Gaussian Inc., Pittsburgh PA, 1995.
    • (1995)
  • 143
    • 33746515339 scopus 로고    scopus 로고
    • Details of comparison between HF, post HF and DFT methods are available
    • Details of comparison between HF, post HF and DFT methods are available 2-44 and will not be repeated here.
  • 166
    • 33746569831 scopus 로고    scopus 로고
    • 51 Kinetic and thermochemical data for the reaction of 1,3diphenylisobenzofuran with various olefins (with and without Lewis-acid catalysis) have been reported.52
    • 51 Kinetic and thermochemical data for the reaction of 1,3diphenylisobenzofuran with various olefins (with and without Lewis-acid catalysis) have been reported.52
  • 175
    • 33746516470 scopus 로고
    • (Chem. Abstr., 1987, 106, 17670); () V. D. Kiselev, V. B. Malkov, G. V. Akhmet-Zyanova and A. I. Konovalov, J. Org. Client. USSR, 1988, 26, 200; (A:) V. D. Kiselev and A. I. Konovalov, Rtiss. Chcm. Rev., 1989, 58, 230
    • V. D. Kiselev, I. M. Shakirov and A. I. Konovalov, Zh. Org. Khim, 1986, 22, 1034 (Chem. Abstr., 1987, 106, 17670); () V. D. Kiselev, V. B. Malkov, G. V. Akhmet-Zyanova and A. I. Konovalov, J. Org. Client. USSR, 1988, 26, 200; (A:) V. D. Kiselev and A. I. Konovalov, Rtiss. Chcm. Rev., 1989, 58, 230;
    • (1986) Zh. Org. Khim , vol.22
    • Kiselev, V.D.1    Shakirov, I.M.2    Konovalov, A.I.3
  • 177
    • 33746520945 scopus 로고
    • (Chem. Abstr., 1989, 111, 231660); (;;) N. R. Adieezakov, V. D. Kiselev and A. I. Konovalov, J. Org. Chem. USSR, 1989, 25, 1033
    • (k) V. D. Kiselev, N. R. Adigezalov and A. I. Konovalov, Zh. Org. Khim., 1989, 25, 539 (Chem. Abstr., 1989, 111, 231660); (;;) N. R. Adieezakov, V. D. Kiselev and A. I. Konovalov, J. Org. Chem. USSR, 1989, 25, 1033;
    • (1989) Zh. Org. Khim. , vol.25
    • Kiselev, V.D.1    Adigezalov, N.R.2    Konovalov, A.I.3
  • 183
    • 33746546958 scopus 로고    scopus 로고
    • For some earlier theoretical studies see réf. 3 (c), 3 (g) and 55.
    • For some earlier theoretical studies see réf. 3 (c), 3 (g) and 55.
  • 187
    • 33746536378 scopus 로고    scopus 로고
    • 56 DFT studies of intramolecular Diels-Alder reactions of amine- and amide-substituted isobenzofurans have been reported recently.12
    • 56 DFT studies of intramolecular Diels-Alder reactions of amine- and amide-substituted isobenzofurans have been reported recently.12
  • 189
    • 33746548129 scopus 로고    scopus 로고
    • Transition state calculations for reaction (1) have already been published.59 Our results (see also réf. 4 (p)) differ in some respects from these data.
    • Transition state calculations for reaction (1) have already been published.59 Our results (see also réf. 4 (p)) differ in some respects from these data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.