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Volumn 75, Issue 22, 2010, Pages 7954-7957

An intramolecular PIFA-mediated metal-free allylic oxycarbonylation reaction and its application to the preparation of furopyrimidinones

Author keywords

[No Author keywords available]

Indexed keywords

C-H ACTIVATION; CARBAMOYL; FUNCTIONALIZATIONS;

EID: 78449243408     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101797s     Document Type: Article
Times cited : (29)

References (45)
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    • See also ref 6
    • See also ref 6.
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    • For some excellent books on the chemistry of hypervalent iodine reagents, see:; VCH: New York
    • For some excellent books on the chemistry of hypervalent iodine reagents, see: Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992.
    • (1992) The Organic Chemistry of Polycoordinated Iodine
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    • Ed.; Springer-Verlag: Berlin, Germany,. For some recent reviews on the same topic, see
    • Wirth, T., Ed. Hypervalent Iodine Chemistry; Springer-Verlag: Berlin, Germany, 2003. For some recent reviews on the same topic, see
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    • For some illustrating overall views on the C-H activation strategy, see
    • For some illustrating overall views on the C-H activation strategy, see: Bergman, R. G. Nature 2007, 446, 391-393.
    • (2007) Nature , vol.446 , pp. 391-393
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    • As expected to the view of several precedents, the yield for this cyclocondensation is markedly diminished when starting from N,N′- disubstituted ureas. This structural feature will be crucial for our synthetic purposes (vide infra)
    • As expected to the view of several precedents, the yield for this cyclocondensation is markedly diminished when starting from N,N′- disubstituted ureas. This structural feature will be crucial for our synthetic purposes (vide infra).
  • 33
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    • For a recent review on heterocyclic synthesis under solvent-free conditions, see
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    • The study was also extended to the use of some other hypervalent iodine reagents (PIDA and IBX), but complex mixtures of compounds were obtained in all cases
    • The study was also extended to the use of some other hypervalent iodine reagents (PIDA and IBX), but complex mixtures of compounds were obtained in all cases.
  • 35
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    • A similar solution was applied in a study related to the intramolecular PIFA-mediated cyclization of N -methoxy- N ′-phenylureas to render 2-benzimidazolinones, which was productive only when an additional N ′-substituent (R) was incorporated to the starting material
    • A similar solution was applied in a study related to the intramolecular PIFA-mediated cyclization of N -methoxy- N ′-phenylureas to render 2-benzimidazolinones, which was productive only when an additional N ′-substituent (R) was incorporated to the starting material. Romero, A. G.; Darlington, W. H.; McMillan, M. W. J. Org. Chem. 1997, 62, 6582-6587
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    • The I(III) mediated intramolecular electrophilic aromatic amidation was first reported by Kikugawa's group and deeply exploited thereafter
    • The I(III) mediated intramolecular electrophilic aromatic amidation was first reported by Kikugawa's group and deeply exploited thereafter. Kawase, M.; Kitamura, T.; Kikugawa, Y. J. Org. Chem. 1989, 3394-3403
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    • A Hofmann rearrangement leading to a 5-aminoDHPM was not observed either
    • A Hofmann rearrangement leading to a 5-aminoDHPM was not observed either.
  • 39
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    • Aryl groups were selected, over other possibilities, on the basis of their known ability to stabilize oxidized amides (acylnitrenium ions). See, for example: In;, Eds.; John Wiley & Sons: Hoboken, NJ,; pp - and references cited therein
    • Aryl groups were selected, over other possibilities, on the basis of their known ability to stabilize oxidized amides (acylnitrenium ions). See, for example: Falvey, D. E. In Reactive Intermediate Chemistry; Moss, R. A.; Platz, M.; Jones, M., Jr., Eds.; John Wiley & Sons: Hoboken, NJ, 2004; pp 593 - 650 and references cited therein.
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    • Metal-catalyzed C-H activation processes accomplished as a result of the generation of stabilized deficient intermediates followed by a 1,5-hydride shift are known. See, for example
    • Metal-catalyzed C-H activation processes accomplished as a result of the generation of stabilized deficient intermediates followed by a 1,5-hydride shift are known. See, for example: Tobisu, M.; Chatani, N. Angew. Chem., Int. Ed. 2006, 45, 1683-1684
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    • This particular behavior, in the context of I(III)-mediated heterocyclic synthesis, was first reported by Kita's group.;, () Later, the preferential formation of lactams over lactones was reached by subtle modification of the amide functional group by Knappp's and Ciufolini's groups:; J. Org. Chem. 1988, 53, 4006-4014
    • This particular behavior, in the context of I(III)-mediated heterocyclic synthesis, was first reported by Kita's group. Tamura, Y.; Yakura, T.; Haruta, J.-I.; Kita, Y. J. Org. Chem. 1987, 52 (2) 3927-3930 Later, the preferential formation of lactams over lactones was reached by subtle modification of the amide functional group by Knappp's and Ciufolini's groups: Knapp, S.; Levorse., A. T. J. Org. Chem. 1988, 53, 4006-4014
    • (1987) J. Org. Chem. , vol.52 , Issue.2 , pp. 3927-3930
    • Tamura, Y.1    Yakura, T.2    Haruta, J.-I.3    Kita, Y.4    Knapp, S.5    Levorse, A.T.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.