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Volumn 61, Issue 25, 1996, Pages 8849-8859

An efficient and simple entry to N-substituted β-enamino acid derivatives from 2-alkyl-2-oxazolines and 2-alkyl-2-thiazolines

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; OXAZOLINE DERIVATIVE; THIAZOLE DERIVATIVE;

EID: 0030469796     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961037y     Document Type: Article
Times cited : (24)

References (101)
  • 22
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    • Reviews: (a) Cole, D. Tetrahedron 1994, 50, 9517. (b) Juaristi, E.; Quintana, D.; Escalante, J. Aldrichimica Acta 1994, 27, 3.
    • (1994) Tetrahedron , vol.50 , pp. 9517
    • Cole, D.1
  • 33
    • 16944365549 scopus 로고
    • Eur. Pat. Nr. 0144980 A2
    • (c) Jolidon, S.; Meul, T. Eur. Pat. Nr. 0144980 A2; Chem. Abstr. 1987, 105, 43325p.
    • (1987) Chem. Abstr. , vol.105 , pp. 43325
    • Jolidon, S.1    Meul, T.2
  • 39
    • 0001208734 scopus 로고
    • Turchi, I., Ed.; Interscience: New York
    • (c) Maryanoff, B. E. Heterocyclic Compounds; Turchi, I., Ed.; Interscience: New York, 1986; Vol. 45, p 963.
    • (1986) Heterocyclic Compounds , vol.45 , pp. 963
    • Maryanoff, B.E.1
  • 66
    • 0342661223 scopus 로고
    • Baldwin, J. E., and Magnus, P. D., Eds.; Pergamon Press: Oxford, U.K., Chapter 7
    • (a) Perlmutter, P. In Conjugate Addtion Reactions in Organic Synthesis; Baldwin, J. E., and Magnus, P. D., Eds.; Pergamon Press: Oxford, U.K., 1992; Chapter 7, p 352.
    • (1992) Conjugate Addtion Reactions in Organic Synthesis , pp. 352
    • Perlmutter, P.1
  • 72
    • 0013623526 scopus 로고
    • Separately, Poindexter described the preparation of these compounds as precursors in the synthesis of 1,4-dihydropyridines. See: Poindexter, G. S.; Catt, J. D.; Sasse, P. A.; Kercher, M. A. Heterocycles 1993, 36, 295.
    • (1993) Heterocycles , vol.36 , pp. 295
    • Poindexter, G.S.1    Catt, J.D.2    Sasse, P.A.3    Kercher, M.A.4
  • 79
    • 0029942721 scopus 로고    scopus 로고
    • Meyers has recently described the synthesis and reactivity in Pd-mediated cross-coupling reactions of chiral 2-bromo-2-oxazolines, a very reactive masked formyl group. See: Meyers, A. I.; Novachek, K. A. Tetrahedron Lett. 1996, 37, 1747.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1747
    • Meyers, A.I.1    Novachek, K.A.2
  • 89
    • 0000838058 scopus 로고
    • The preparation of such compounds, using the thionyl chloride method, requires purification of the crude reaction by distillation. In these cases, a partial thermal decomposition affording the corresponding nitriles and alkylhalides has been observed (von Braun reaction). See: Vaughan, W.; Carlson, D. R. J. Am. Chem. Soc. 1962, 84, 769. Therefore, the Uneyama method (ref 27) was the only procedure applied for obtaining these derivatives.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 769
    • Vaughan, W.1    Carlson, D.R.2
  • 90
    • 84889513911 scopus 로고    scopus 로고
    • note
    • In most instances, small amounts of amides resulting from the hydrolysis of unreacted imidoyl chlorides (7) were identified in the crude mixture of the reaction. These byproducts were easily separated by flash chromatography.
  • 91
    • 84889506496 scopus 로고    scopus 로고
    • note
    • In contrast with other related processes (ref 21), bases, such as n-butyl lithium, cannot be used in this reaction due to the high reactivity of the imidoyl halides toward nucleophiles. See also refs 28 and 29.
  • 92
    • 84889546842 scopus 로고    scopus 로고
    • note
    • Similar hydrogen bond interactions have been observed for related systems. (a) See, e.g., refs 20c, 21, 22.
  • 96
    • 84889515326 scopus 로고    scopus 로고
    • note
    • 1H NMR in the crude mixture of the reaction.
  • 99
    • 37049087023 scopus 로고
    • To the best of our knowledge, only one example with a similar structure, obtained by a [2 + 2] cycloaddition reaction of an oxazolinyl alkylamide with dimethyl fumarate, has been reported. See: Ghose, S.; Gilchrist, T. L. J. Chem. Soc., Perkin Trans 1, 1991,775.
    • (1991) J. Chem. Soc., Perkin Trans 1 , pp. 775
    • Ghose, S.1    Gilchrist, T.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.