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Volumn 76, Issue 9, 2011, Pages 3203-3221

Regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles via [3,3] or [1,3] rearrangements of O-vinyl oximes

Author keywords

[No Author keywords available]

Indexed keywords

ENOLIZATION; MECHANISTIC PATHWAYS; REGIOSELECTIVE SYNTHESIS; SIGMATROPIC REARRANGEMENTS;

EID: 79955568372     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200061b     Document Type: Article
Times cited : (81)

References (143)
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    • The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles
    • John Wiley & Sons: Hoboken
    • For a review and examples of the Vilsmeier reaction, see: Jones, G.; Stanforth, S. P. " The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles. In Organic Reactions; John Wiley & Sons: Hoboken, 1997; Vol. 49, p 1.
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    • For examples of [1,3] rearrangements and ring-contractions of allyl vinyl ethers, see: Nasveschuk, C. G.; Rovis, T. Org. Lett. 2005, 7, 2173
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    • Nasveschuk, C.G.1    Rovis, T.2
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    • note
    • For examples of regioisomeric mixtures of products obtained from the use of terminal alkynes in the Trofimov reaction see
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    • For related syntheses of allyl vinyl ethers which undergo subsequent Claisen rearrangements, see: Wang, K.; Bungard, C. J.; Nelson, S. G. Org. Lett. 2007, 9, 2325
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    • 1H NOESY experiments were used for further verification.
    • 1H NOESY experiments were used for further verification.
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    • Compounds 3d, 3e, 3f, and 3i were reported in our previous communication. See ref 24.
    • Compounds 3d, 3e, 3f, and 3i were reported in our previous communication. See ref 24.
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    • These substrates gave low yields or no conversion when run under the same reaction conditions at 25 °C.
    • These substrates gave low yields or no conversion when run under the same reaction conditions at 25 °C.
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    • The regiochemistry of pyrroles 4a, 4b, and 4m-v was misrepresented in our previous communication. (24)
    • The regiochemistry of pyrroles 4a, 4b, and 4m-v was misrepresented in our previous communication. (24)
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    • Less than 5% of 2 and the corresponding ketone were isolated with the pyrrole products. The remainder of the starting material is most likely converted into a highly colored polymeric material which remains physisorbed to silica gel.
    • Less than 5% of 2 and the corresponding ketone were isolated with the pyrrole products. The remainder of the starting material is most likely converted into a highly colored polymeric material which remains physisorbed to silica gel.
  • 118
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    • The proposed mechanism for 3-cyano-4-methylpyrrole formation is based on analogous mechanisms determined and proposed for the Fisher indole and Trofimov reactions. See refs 15f, 20c, and 20d.
    • The proposed mechanism for 3-cyano-4-methylpyrrole formation is based on analogous mechanisms determined and proposed for the Fisher indole and Trofimov reactions. See refs 15f, 20c, and 20d.
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    • Attempts at isolation of 5s by silica gel chromatography led to the isolation of 4s.
    • Attempts at isolation of 5s by silica gel chromatography led to the isolation of 4s.
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    • Solvent choice showed little effect on the base-promoted rearrangement and cyclization of 2b to 3b.
    • Solvent choice showed little effect on the base-promoted rearrangement and cyclization of 2b to 3b.
  • 122
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    • See the Supporting Information for a comparison of NMR data to literature values.
    • See the Supporting Information for a comparison of NMR data to literature values.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.