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Volumn 130, Issue 5, 2008, Pages 1558-1559

Orthogonal synthesis of indolines and isoquinolines via aryne annulation

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; INDOLE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PAPAVERINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

EID: 38949175721     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0780582     Document Type: Article
Times cited : (217)

References (50)
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    • For reviews on the use of arynes in organic synthesis, see: a, Trost, B. M, Fleming, I, Eds, Pergamon Press: New York
    • For reviews on the use of arynes in organic synthesis, see: (a) Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 483-515.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 483-515
    • Kessar, S.V.1
  • 10
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    • For examples of aryne annulation approaches to the synthesis of heterocycles, see: (a) Nair, V, Kim, K. H. J. Org. Chem. 1975, 40, 3784-3786
    • For examples of aryne annulation approaches to the synthesis of heterocycles, see: (a) Nair, V.; Kim, K. H. J. Org. Chem. 1975, 40, 3784-3786.
  • 14
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    • For recent examples of metal-free syntheses of benzannulated heterocycles, see: (a) Movassaghi, M.; Hill, M. D. J. Am. Chem. Soc. 2006, 128, 14254-14255.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 14254-14255
    • Movassaghi, M.1    Hill, M.D.2
  • 18
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    • For a facile two-step preparation of o-silylaryl triflates from the corresponding o-bromophenols, see: Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454-1458.
    • (b) For a facile two-step preparation of o-silylaryl triflates from the corresponding o-bromophenols, see: Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454-1458.
  • 19
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    • For examples of [3+2] cycloadditions with arynes, see: (a) Del Mazza, D.; Reinecke, M. G. J. Chem. Soc., Chem. Commun. 1981, 124-125.
  • 25
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    • For results highlighting aryne regioselectivity, see: a
    • For results highlighting aryne regioselectivity, see: (a) Xin, H. Y.; Biehl, E. R. J. Org. Chem. 1983, 48, 4397-4399.
    • (1983) J. Org. Chem , vol.48 , pp. 4397-4399
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  • 28
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    • For computational studies of aryne electronic properties, see
    • For computational studies of aryne electronic properties, see: Johnson, W. T. G.; Cramer, C. J. J. Am. Chem. Soc. 2001, 123, 923-928.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 923-928
    • Johnson, W.T.G.1    Cramer, C.J.2
  • 29
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    • For other examples of direct indoline synthesis, see: a
    • For other examples of direct indoline synthesis, see: (a) Yip, K.-T.; Yang, M.; Law, K.-L.; Zhu, N.-Y.; Yang, D. J. Am. Chem. Soc. 2006, 128, 3130-3131.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 3130-3131
    • Yip, K.-T.1    Yang, M.2    Law, K.-L.3    Zhu, N.-Y.4    Yang, D.5
  • 32
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    • For classical syntheses of isoquinolines, see: a
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  • 37
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    • Attempts to expand the substrate scope by simply employing N-vinyl acetamide met with exclusive arylation at the enamine olefin terminus, see: Ramtohul, Y. K.; Chartrand, A. Org. Lett. 2007, 9, 1029-1032.
    • Attempts to expand the substrate scope by simply employing N-vinyl acetamide met with exclusive arylation at the enamine olefin terminus, see: Ramtohul, Y. K.; Chartrand, A. Org. Lett. 2007, 9, 1029-1032.
  • 38
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    • Isolation of papaverine: Merck, G
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    • (1848) Liebigs Ann. Chem , vol.66 , pp. 125-128
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    • (1998) The Isoquinoline Alkaloids , pp. 107-122
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    • Decarboxylated products of this type (e.g, 6) constitute those originally targeted in the N-vinyl acetamide case see ref 15, thereby circumventing the undesired ene reactivity previously displayed by these substrates
    • Decarboxylated products of this type (e.g., 6) constitute those originally targeted in the N-vinyl acetamide case (see ref 15), thereby circumventing the undesired ene reactivity previously displayed by these substrates.


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