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Volumn 53, Issue 26, 1997, Pages 8853-8870

A novel method for suppression of the abnormal Fischer indole synthesis

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXAZINE DERIVATIVE; INDOLE; INDOLE DERIVATIVE; PRIANOSIN D; PYRROLO[1,2 A]QUINOLINE DERIVATIVE;

EID: 0030835777     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)90396-3     Document Type: Article
Times cited : (27)

References (44)
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    • Nishiyama, S.1    Cheng, J.2    Tao, X.L.3    Yamamura, S.4
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    • Total Syntheses of Discorhabdin C: a. Nishiyama, S.; Cheng, J.; Tao, X. L.; Yamamura, S. Tetrahedron Lett. 1991, 32, 4151. b. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem. Soc. 1992, 114, 2175. Tao, X. L.; Cheng, J.; Nishiyama, S.; Yamamura, S.; Tetrahedron 1994, 50, 2017.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2175
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  • 7
    • 30644469804 scopus 로고
    • Total Syntheses of Discorhabdin C: a. Nishiyama, S.; Cheng, J.; Tao, X. L.; Yamamura, S. Tetrahedron Lett. 1991, 32, 4151. b. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem. Soc. 1992, 114, 2175. Tao, X. L.; Cheng, J.; Nishiyama, S.; Yamamura, S.; Tetrahedron 1994, 50, 2017.
    • (1994) Tetrahedron , vol.50 , pp. 2017
    • Tao, X.L.1    Cheng, J.2    Nishiyama, S.3    Yamamura, S.4
  • 8
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    • Formal syntheses of Discorhabdin C: a. White, J. D.; Yager, K. M.; Yakura, T. J. Am. Chem. Soc. 1994, 116, 1831. b. Sandanandan, E. U.; Pillai, S. K.; Lakshmikantham, M. V.; Billimoria, A. D.; Culpepper, J. S.; Cava, M. P. J. Org. Chem. 1995, 60, 1800.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1831
    • White, J.D.1    Yager, K.M.2    Yakura, T.3
  • 16
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    • Total syntheses of Makaluvamine D: a. White, J. D.; Yager, K. M.; Yakura, T. J. Am. Chem. Soc. 1994, 116, 1831. b. Sandanandan, E. U.; Pillai, S. K.; Lakshmikantham, M. V.; Billimoria, A. D.; Culpepper, J. S.; Cava, M. P. J. Org. Chem. 1995, 60, 1800.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1831
    • White, J.D.1    Yager, K.M.2    Yakura, T.3
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    • Total syntheses of Damirone B: a. Sadanandan, E. V.; Cava, M. P. Tetrahedron Lett. 1993, 34, 2405. b. Baumann, C.; Bröckelmann, M.; Fugmann, B.; Steffan, B.; Steglich, W.; Sheldrick, W. S. Angew. Chem. Int. Ed. Engl. 1993, 32, 1087.
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  • 21
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    • Reviews of the Fischer indole synthesis: a. Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 607. b. Robinson, B. The Fischer Indole Synthesis, Wiley: New York, 1982.
    • (1993) Org. Prep. Proced. Int. , vol.25 , pp. 607
    • Hughes, D.L.1
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    • Wiley: New York
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    • (1982) The Fischer Indole Synthesis
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    • A hydrazone of 2-methoxy-5-nitrophenylhydrazine was reported to smoothly undergo the Fischer indole synthesis using 5-sulfosalicylic acid as the proton source. Vinograd, L. K.; Suvorov, N. N. Khim. Geterot. Soedin. (English trans.) 1984, 1206. p-Toluenesulfonic acid gave similar results in our hands.
    • (1984) Khim. Geterot. Soedin. (English Trans.) , pp. 1206
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  • 29
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    • note
    • Structure 17 is a generic structure intended to illustrate the kinds of byproducts obtained in such reactions and does not represent an actual byproduct that we have isolated and characterized.
  • 34
    • 0343246854 scopus 로고    scopus 로고
    • note
    • A reviewer has suggested that the successful cyclization of 23, compared to 5 and 11, might be due to the fact that 23 is a single stereoisomer, whereas 5 and 11 are mixtures of E and Z isomers about the C=N bond. We cannot rule out this possibility, and indeed, the yield of indole in the case of 5, 11, and 23 (11%, 30%, 82%) might correlate with the observed diastereomeric ratios of 3:1, 2:1, >20:1, if one assumes the minor isomers in the case of 5 and 11 have the same configuration as the sole observed isomer of 23. However, this rationale is not in accord with the generally accepted mechanism of the Fischer indole reaction, which is believed to involve tautomerization to the diprotonated enamine. In other words, both E and Z hydrazones would give the same diprotonated enamine. For this reason, we think it unlikely that the differences observed are due to the differences in diastereomeric ratios observed with the different hydrazones.


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