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Volumn 68, Issue 8, 2003, Pages 3299-3302

Regiochemical switching in Diels-Alder cycloadditions by change in oxidation state of removable diene sulfur substituents. Synthesis of carbazoles by sequential heteroannulation and Diels-Alder cycloaddition

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION REACTIONS; HETEROANNULATION;

EID: 0037453689     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0268714     Document Type: Article
Times cited : (34)

References (18)
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    • For other examples of nitrogen heterocycles prepared by heteroannulation of aryl halides with dienes, see: (a) Larock, R. C.; Berrios-Pefia, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. (b) Larock, R. C.; Guo, L. Synlett 1995, 465. (c) Larock, R. C.; Berrios-Peña, N. G.; Fried, C, A.; Yum, E. K.; Tu, C.; Leong, W. J. Org. Chem. 1993, 58, 4509. (d) O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.
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    • For other examples of nitrogen heterocycles prepared by heteroannulation of aryl halides with dienes, see: (a) Larock, R. C.; Berrios-Pefia, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. (b) Larock, R. C.; Guo, L. Synlett 1995, 465. (c) Larock, R. C.; Berrios-Peña, N. G.; Fried, C, A.; Yum, E. K.; Tu, C.; Leong, W. J. Org. Chem. 1993, 58, 4509. (d) O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.
    • (1995) Synlett , pp. 465
    • Larock, R.C.1    Guo, L.2
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    • For other examples of nitrogen heterocycles prepared by heteroannulation of aryl halides with dienes, see: (a) Larock, R. C.; Berrios-Pefia, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. (b) Larock, R. C.; Guo, L. Synlett 1995, 465. (c) Larock, R. C.; Berrios-Peña, N. G.; Fried, C, A.; Yum, E. K.; Tu, C.; Leong, W. J. Org. Chem. 1993, 58, 4509. (d) O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.
    • (1993) J. Org. Chem. , vol.58 , pp. 4509
    • Larock, R.C.1    Berrios-Peña, N.G.2    Fried, C.A.3    Yum, E.K.4    Tu, C.5    Leong, W.6
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    • For other examples of nitrogen heterocycles prepared by heteroannulation of aryl halides with dienes, see: (a) Larock, R. C.; Berrios-Pefia, N.; Narayanan, K. J. Org. Chem. 1990, 55, 3447. (b) Larock, R. C.; Guo, L. Synlett 1995, 465. (c) Larock, R. C.; Berrios-Peña, N. G.; Fried, C, A.; Yum, E. K.; Tu, C.; Leong, W. J. Org. Chem. 1993, 58, 4509. (d) O'Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.
    • (1983) J. Org. Chem. , vol.48 , pp. 807
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    • For selected reviews of carbazoles, see: (a) Moody, C. J. Synlett 1994, 681. (b) Misra, N.; Luthra, R.; Singh, K. L.; Kumar, S. In Comprehensive Natural Products Chemistry; Kelly, J. W., Ed.; Elsevier: Amsterdam, 1999; Vol. 4, p 54. (c) Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Eds.; Springer-Verlag: Wien, 1977; Vol. 34, pp 299-371. (d) Bhattacharyya, P.; Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1987; Vol. 52, pp 159-209. (e) Chakraborty, D. P.; Roy, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Steglich, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1991; Vol. 57, pp 71-152.
    • (1994) Synlett , pp. 681
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    • Kelly, J. W., Ed.; Elsevier: Amsterdam
    • For selected reviews of carbazoles, see: (a) Moody, C. J. Synlett 1994, 681. (b) Misra, N.; Luthra, R.; Singh, K. L.; Kumar, S. In Comprehensive Natural Products Chemistry; Kelly, J. W., Ed.; Elsevier: Amsterdam, 1999; Vol. 4, p 54. (c) Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Eds.; Springer-Verlag: Wien, 1977; Vol. 34, pp 299-371. (d) Bhattacharyya, P.; Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1987; Vol. 52, pp 159-209. (e) Chakraborty, D. P.; Roy, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Steglich, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1991; Vol. 57, pp 71-152.
    • (1999) Comprehensive Natural Products Chemistry , vol.4 , pp. 54
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    • Herz, W., Grisebach, H., Kirby, G. W., Eds.; Springer-Verlag: Wien
    • For selected reviews of carbazoles, see: (a) Moody, C. J. Synlett 1994, 681. (b) Misra, N.; Luthra, R.; Singh, K. L.; Kumar, S. In Comprehensive Natural Products Chemistry; Kelly, J. W., Ed.; Elsevier: Amsterdam, 1999; Vol. 4, p 54. (c) Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Eds.; Springer-Verlag: Wien, 1977; Vol. 34, pp 299-371. (d) Bhattacharyya, P.; Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1987; Vol. 52, pp 159-209. (e) Chakraborty, D. P.; Roy, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Steglich, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1991; Vol. 57, pp 71-152.
    • (1977) Progress in the Chemistry of Organic Natural Products , vol.34 , pp. 299-371
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    • Herz, W., Grisebach, H., Kirby, G. W., Tamm, C., Eds.; Springer-Verlag: Wien
    • For selected reviews of carbazoles, see: (a) Moody, C. J. Synlett 1994, 681. (b) Misra, N.; Luthra, R.; Singh, K. L.; Kumar, S. In Comprehensive Natural Products Chemistry; Kelly, J. W., Ed.; Elsevier: Amsterdam, 1999; Vol. 4, p 54. (c) Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Eds.; Springer-Verlag: Wien, 1977; Vol. 34, pp 299-371. (d) Bhattacharyya, P.; Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1987; Vol. 52, pp 159-209. (e) Chakraborty, D. P.; Roy, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Steglich, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1991; Vol. 57, pp 71-152.
    • (1987) Progress in the Chemistry of Organic Natural Products , vol.52 , pp. 159-209
    • Bhattacharyya, P.1    Chakraborty, D.P.2
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    • Herz, W., Kirby, G. W., Steglich, G. W., Tamm, C., Eds.; Springer-Verlag: Wien
    • For selected reviews of carbazoles, see: (a) Moody, C. J. Synlett 1994, 681. (b) Misra, N.; Luthra, R.; Singh, K. L.; Kumar, S. In Comprehensive Natural Products Chemistry; Kelly, J. W., Ed.; Elsevier: Amsterdam, 1999; Vol. 4, p 54. (c) Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Eds.; Springer-Verlag: Wien, 1977; Vol. 34, pp 299-371. (d) Bhattacharyya, P.; Chakraborty, D. P. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1987; Vol. 52, pp 159-209. (e) Chakraborty, D. P.; Roy, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Steglich, G. W., Tamm, C., Eds.; Springer-Verlag: Wien, 1991; Vol. 57, pp 71-152.
    • (1991) Progress in the Chemistry of Organic Natural Products , vol.57 , pp. 71-152
    • Chakraborty, D.P.1    Roy, S.2
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    • Wiley: Chichester, UK, Chapter 4
    • For the effects of electron-withdrawing/donating substituents on the reglochemistry of Diels-Alder reactions, see: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: Chichester, UK, 1976; Chapter 4.
    • (1976) Frontier Orbitals and Organic Chemical Reactions
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    • Negodyaev, N. D.; Pushkareva, Z. V. Khim. Geterotsikl. Soedin. 1967, 60; Chem. Abstr. 1969, 70, 87443.
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