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Volumn , Issue 6, 2004, Pages 991-994

New persistent heteroarylmethyl radicals resulting from the intramolecular addition of aryloxymethyl radicals onto ketenimines. Synthesis of 2H-1,4-benzoxazines

Author keywords

1,4 benzoxazines; Aryloxymethyl radical; Cyclization; Ketenimine; Persistent

Indexed keywords

BENZOXAZINE DERIVATIVE; ETHER DERIVATIVE; IMINE; METHYL GROUP; RADICAL; SILANE DERIVATIVE; TRIS(TRIMETHYLSILYL)SILANE; UNCLASSIFIED DRUG;

EID: 3142764452     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822883     Document Type: Article
Times cited : (24)

References (43)
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    • For a seminal paper in which the PRE was recognized see: (a) Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925. (b) For the naming of the principle of PRE see: Daikh, B. E.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 2938. (c) For an excellent review on the PRE see: Fischer, H. Chem. Rev. 2001, 101, 3581. (d) For examples of PRE in organic synthesis see: Studer, A. Angew. Chem. Int. Ed. 2000, 39, 1108. (e) Wetter, C.; Jantos, K.; Woithe, K.; Studer, A. Org. Lett. 2003, 5, 2899. (f) Studer, A. Chem.-Eur. J. 2001, 7, 1159. (g) Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079. (h) Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell, T. T. J. Org. Chem. 2001, 66, 5759. (i) Wetter, C.; Studer, A. Chem. Commun. 2004, 174.
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    • For a seminal paper in which the PRE was recognized see: (a) Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925. (b) For the naming of the principle of PRE see: Daikh, B. E.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 2938. (c) For an excellent review on the PRE see: Fischer, H. Chem. Rev. 2001, 101, 3581. (d) For examples of PRE in organic synthesis see: Studer, A. Angew. Chem. Int. Ed. 2000, 39, 1108. (e) Wetter, C.; Jantos, K.; Woithe, K.; Studer, A. Org. Lett. 2003, 5, 2899. (f) Studer, A. Chem.-Eur. J. 2001, 7, 1159. (g) Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079. (h) Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell, T. T. J. Org. Chem. 2001, 66, 5759. (i) Wetter, C.; Studer, A. Chem. Commun. 2004, 174.
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    • For a seminal paper in which the PRE was recognized see: (a) Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925. (b) For the naming of the principle of PRE see: Daikh, B. E.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 2938. (c) For an excellent review on the PRE see: Fischer, H. Chem. Rev. 2001, 101, 3581. (d) For examples of PRE in organic synthesis see: Studer, A. Angew. Chem. Int. Ed. 2000, 39, 1108. (e) Wetter, C.; Jantos, K.; Woithe, K.; Studer, A. Org. Lett. 2003, 5, 2899. (f) Studer, A. Chem.-Eur. J. 2001, 7, 1159. (g) Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079. (h) Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell, T. T. J. Org. Chem. 2001, 66, 5759. (i) Wetter, C.; Studer, A. Chem. Commun. 2004, 174.
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    • Leroi, C.1    Fenet, B.2    Couturier, J.-L.3    Guerret, O.4    Ciufolini, M.A.5
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    • For a seminal paper in which the PRE was recognized see: (a) Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925. (b) For the naming of the principle of PRE see: Daikh, B. E.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 2938. (c) For an excellent review on the PRE see: Fischer, H. Chem. Rev. 2001, 101, 3581. (d) For examples of PRE in organic synthesis see: Studer, A. Angew. Chem. Int. Ed. 2000, 39, 1108. (e) Wetter, C.; Jantos, K.; Woithe, K.; Studer, A. Org. Lett. 2003, 5, 2899. (f) Studer, A. Chem.-Eur. J. 2001, 7, 1159. (g) Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079. (h) Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell, T. T. J. Org. Chem. 2001, 66, 5759. (i) Wetter, C.; Studer, A. Chem. Commun. 2004, 174.
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    • 1642439238 scopus 로고    scopus 로고
    • For a seminal paper in which the PRE was recognized see: (a) Fischer, H. J. Am. Chem. Soc. 1986, 108, 3925. (b) For the naming of the principle of PRE see: Daikh, B. E.; Finke, R. G. J. Am. Chem. Soc. 1992, 114, 2938. (c) For an excellent review on the PRE see: Fischer, H. Chem. Rev. 2001, 101, 3581. (d) For examples of PRE in organic synthesis see: Studer, A. Angew. Chem. Int. Ed. 2000, 39, 1108. (e) Wetter, C.; Jantos, K.; Woithe, K.; Studer, A. Org. Lett. 2003, 5, 2899. (f) Studer, A. Chem.-Eur. J. 2001, 7, 1159. (g) Leroi, C.; Fenet, B.; Couturier, J.-L.; Guerret, O.; Ciufolini, M. A. Org. Lett. 2003, 5, 1079. (h) Allen, A. D.; Fenwick, M. F.; Henry-Riyad, H.; Tidwell, T. T. J. Org. Chem. 2001, 66, 5759. (i) Wetter, C.; Studer, A. Chem. Commun. 2004, 174.
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    • 7
    • 7 (b) Alajarín, M.; Vidal, A.; Tovar, F.; Ramírez de Arellano, M. C.; Cossío, F. P.; Arrieta, A.; Lecea, B. J. Org. Chem. 2000, 65, 3633. (c) Alajarín, M.; Vidal, A.; Ortín, M.-M. Synthesis 2002, 2393; and references cited therein.
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    • and references cited therein
    • 7 (b) Alajarín, M.; Vidal, A.; Tovar, F.; Ramírez de Arellano, M. C.; Cossío, F. P.; Arrieta, A.; Lecea, B. J. Org. Chem. 2000, 65, 3633. (c) Alajarín, M.; Vidal, A.; Ortín, M.-M. Synthesis 2002, 2393; and references cited therein.
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  • 38
    • 3142746982 scopus 로고    scopus 로고
    • note
    • 2O: C, 74.90; H, 5.28; N, 6.99. Found: C, 74.76; H, 5.18; N, 7.08.
  • 39
    • 3142735217 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the structure 10a have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 229317. Copies of the data can be obtained on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (e-mail: deposit@ccdc.cam.ac.uk).
  • 40
    • 0035528865 scopus 로고    scopus 로고
    • For articles dealing with persistent nitrogen-centered radicals see: (a) Nakatsuji, M.; Miura, Y.; Teki, Y. J. Chem. Soc., Perkin Trans. 2 2001, 738. (b) Miura, Y.; Momoki, M.; Fuchikami, T.; Teki, Y.; Itoh, K.; Mizutani, H. J. Org. Chem. 1996, 61, 4300. (c) Roberts, J. R.; Ingold, K. U. J. Am. Chem. Soc. 1973, 95, 3228. (d) Griller, D.; Mendenhall, G. D.; van Hoof, W.; Ingold, K. U. J. Am. Chem. Soc. 1974, 96, 6068.
    • (2001) J. Chem. Soc., Perkin Trans. 2 , pp. 738
    • Nakatsuji, M.1    Miura, Y.2    Teki, Y.3
  • 41
    • 0000455348 scopus 로고    scopus 로고
    • For articles dealing with persistent nitrogen-centered radicals see: (a) Nakatsuji, M.; Miura, Y.; Teki, Y. J. Chem. Soc., Perkin Trans. 2 2001, 738. (b) Miura, Y.; Momoki, M.; Fuchikami, T.; Teki, Y.; Itoh, K.; Mizutani, H. J. Org. Chem. 1996, 61, 4300. (c) Roberts, J. R.; Ingold, K. U. J. Am. Chem. Soc. 1973, 95, 3228. (d) Griller, D.; Mendenhall, G. D.; van Hoof, W.; Ingold, K. U. J. Am. Chem. Soc. 1974, 96, 6068.
    • (1996) J. Org. Chem. , vol.61 , pp. 4300
    • Miura, Y.1    Momoki, M.2    Fuchikami, T.3    Teki, Y.4    Itoh, K.5    Mizutani, H.6
  • 42
    • 0001277929 scopus 로고
    • For articles dealing with persistent nitrogen-centered radicals see: (a) Nakatsuji, M.; Miura, Y.; Teki, Y. J. Chem. Soc., Perkin Trans. 2 2001, 738. (b) Miura, Y.; Momoki, M.; Fuchikami, T.; Teki, Y.; Itoh, K.; Mizutani, H. J. Org. Chem. 1996, 61, 4300. (c) Roberts, J. R.; Ingold, K. U. J. Am. Chem. Soc. 1973, 95, 3228. (d) Griller, D.; Mendenhall, G. D.; van Hoof, W.; Ingold, K. U. J. Am. Chem. Soc. 1974, 96, 6068.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 3228
    • Roberts, J.R.1    Ingold, K.U.2
  • 43
    • 0000339521 scopus 로고
    • For articles dealing with persistent nitrogen-centered radicals see: (a) Nakatsuji, M.; Miura, Y.; Teki, Y. J. Chem. Soc., Perkin Trans. 2 2001, 738. (b) Miura, Y.; Momoki, M.; Fuchikami, T.; Teki, Y.; Itoh, K.; Mizutani, H. J. Org. Chem. 1996, 61, 4300. (c) Roberts, J. R.; Ingold, K. U. J. Am. Chem. Soc. 1973, 95, 3228. (d) Griller, D.; Mendenhall, G. D.; van Hoof, W.; Ingold, K. U. J. Am. Chem. Soc. 1974, 96, 6068.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 6068
    • Griller, D.1    Mendenhall, G.D.2    Van Hoof, W.3    Ingold, K.U.4


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