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Volumn , Issue 1, 2009, Pages 59-62

Tandem Meinwald rearrangement-Fischer indolisation: A one-pot conversion of epoxides into indoles

Author keywords

Aldehydes; Epoxides; Indoles; Rearrangements; Tandem reactions

Indexed keywords


EID: 62349125662     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087476     Document Type: Article
Times cited : (35)

References (32)
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    • and references cited therein. For recent examples, see: a
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    • (2005) Acc. Chem. Res , vol.38 , pp. 851
    • Taylor, R.J.K.1    Reid, M.2    Foot, J.S.3    Raw, S.A.4
  • 6
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    • For a review, see: Rickborn, B. In Comprehensive Organic Synthesis, 3; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 733.
    • (b) For a review, see: Rickborn, B. In Comprehensive Organic Synthesis, Vol. 3; Trost, B. M.; Fleming, I.; Pattenden, G., Eds.; Pergamon: Oxford, 1991, 733.
  • 7
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    • For recent examples, see: (a) Maruoka, K.; Murase, N.; Bureau, R.; Ooi, T.; Yamamoto, H. Tetrahedron 1994, 50, 3663.
    • For recent examples, see: (a) Maruoka, K.; Murase, N.; Bureau, R.; Ooi, T.; Yamamoto, H. Tetrahedron 1994, 50, 3663.
  • 15
    • 0037020824 scopus 로고    scopus 로고
    • and references cited therein. For a review, see
    • (d) For a review, see: Silva, L. F. Jr. Tetrahedron 2002, 58, 9137; and references cited therein.
    • (2002) Tetrahedron , vol.58 , pp. 9137
    • Silva Jr., L.F.1
  • 19
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    • Katritzky, A. R, Ramsden, C. A, Scriven, E. F. V, Taylor, R. J. K, Eds, Elsevier: Oxford, Chap. 3.04; and references therein
    • D'Ischia, M.; Napolitano, A.; Pezzella, A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008, Chap. 3.04; and references therein.
    • (2008) Comprehensive Heterocyclic Chemistry III
    • D'Ischia, M.1    Napolitano, A.2    Pezzella, A.3
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    • For recent reviews, see: (a) Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 607.
    • (1993) Org. Prep. Proced. Int , vol.25 , pp. 607
    • Hughes, D.L.1
  • 28
    • 62349135217 scopus 로고    scopus 로고
    • All novel compounds were fully characterized. 3-(2prime;-Benzofuranyl) indole (6a) Pale orange microcrystals; mp 162-163°C (heptane, Rf, 0.27 (PE-Et2O, 4:1, 1H NMR (400 MHz, CDCl3, δ, 8.33 (br s, 1 H, 8.05-8.00 (m, 1 H, 7.71 (d, J, 2.5 Hz, 1 H, 7.57-7.52 (m, 1 H, 7.49-7.45 (m, 1 H, 7.44-7.39 (m, 1 H, 7.29-7.24 (m, 2 H, 7.23-7.16 (m, 2 H, 6.91 (s, 1 H, 13C NMR (100 MHz, CDCl3, δ, 154.0, 152.9, 136.6, 129.9, 124.6, 123.3, 123.12, 123.08, 122.8, 121.1, 120.4, 120.3, 111.7, 110.8, 108.8, 99.7. IR (neat, νmax, 3399, 2918, 2850, 1623, 1453, 1427, 1358, 1249, 1100 cm-1. MS (EI, m/z, 233 (97, M, 135 (38, 97 (37, 95 (50, 93 (37, 91 (52, 83 (37, 81 (63, 79 (50, 71 (51, 69 (71, 67 (100, 57 (73, 55 (91, 43 (48, 41 (52, HRMS EI, m/z calcd for C16H11NO: 233.0
    • +] (1.5 ppm error)].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.