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Volumn 60, Issue 12, 2007, Pages 898-904

Synthesis of 5-aryloxazolidines via 1,3-dipolar cycloaddition reaction of a non-stabilized azomethine ylide with aromatic aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALDEHYDES; CYCLOADDITION; SYNTHESIS (CHEMICAL);

EID: 36749062555     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH07282     Document Type: Article
Times cited : (29)

References (36)
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  • 7
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    • Ed. A. Padwa, Vols, Wiley-Interscience: New York, NY
    • 3-Dipolar Cycloaddition Chemistry (Ed. A. Padwa) 1984, Vols 1, 2 (Wiley-Interscience: New York, NY).
    • (1984) 3-Dipolar Cycloaddition Chemistry , vol.1-2
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    • For a recent review, see: L. M. Harwood, R. J. Vickers, in Synthetic. Applications of 1,3-Dipolar Cycloaddition Chemistry TowardHeterocycles and Natural Products in Chemistry ofHeterocyclic Compounds (Eds A. Padwa, W. H. Pearson) 2003, 59, Ch. 3, pp. 169-252 (Wiley: New York, NY).
    • For a recent review, see: L. M. Harwood, R. J. Vickers, in Synthetic. Applications of 1,3-Dipolar Cycloaddition Chemistry TowardHeterocycles and Natural Products in Chemistry ofHeterocyclic Compounds (Eds A. Padwa, W. H. Pearson) 2003, Vol. 59, Ch. 3, pp. 169-252 (Wiley: New York, NY).
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    • doi:10.1021/JO00378A013
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    • (1987) J. Org. Chem , vol.52 , pp. 235
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  • 24
    • 85153984508 scopus 로고    scopus 로고
    • The oxazolidine products are unstable under electron-impact ionization conditions and show very low-intensity or no M+ ions. For those compounds that didn't show M+ ions, high-resolution mass spectrometry (electron impact) were obtained on [M, H, see: J. Xu, G. Zuo, Rapid Commun. Mass Spectrom. 2003, 17, 1651 ;
    • + (see: J. Xu, G. Zuo, Rapid Commun. Mass Spectrom. 2003, 17, 1651 ;
  • 25
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    • +. fragment ions.
    • +. fragment ions.
  • 26
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    • 1H NMR analysis of the crude product. The lower yields obtained in some cases, e.g. 75% for lb (entry 2), were due to losses during chromatographic purification of the crude product. The purification was automated and not optimized for each product.
    • 1H NMR analysis of the crude product. The lower yields obtained in some cases, e.g. 75% for lb (entry 2), were due to losses during chromatographic purification of the crude product. The purification was automated and not optimized for each product.
  • 27
    • 0029836113 scopus 로고    scopus 로고
    • For an example of a nitrile acting as a dipolarophile with an azomethine ylide, see:, doi:10.1021/JA9614833
    • For an example of a nitrile acting as a dipolarophile with an azomethine ylide, see: C. W. Derstine, D.N. Smith, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1996, 118, 8485. doi:10.1021/JA9614833
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 8485
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    • F. Hibbert, J. Emsley, in Advances in Physical Organic Chemistry (Ed. D. Bethell) 1990, 26, pp. 255-379 (Academic Press Limited: London).
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    • We thank a referee for pointing out a related example of α-alkylation of a ketone with ylide 4a [M. Rudus, I. Fejes, M. Nyerges, A. Szöllõzy, L. Tokë, P. Groundwater, J. Chem. Soc, Perkin Trans. 1 1999, 1167
    • We thank a referee for pointing out a related example of α-alkylation of a ketone with ylide 4a [M. Rudus, I. Fejes, M. Nyerges, A. Szöllõzy, L. Tokë, P. Groundwater, J. Chem. Soc., Perkin Trans. 1 1999, 1167].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.