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Volumn 10, Issue 22, 2008, Pages 5111-5114

Sustainable synthetic methods: Domino construction of dihydropyridin-4-ones and β-amino esters in aqueous ethanol

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE; 1,4-DIHYDROPYRIDINE; ALCOHOL; DIHYDROPYRIDINE DERIVATIVE; ESTER; UNCLASSIFIED DRUG; WATER;

EID: 58149177442     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801911f     Document Type: Article
Times cited : (60)

References (29)
  • 1
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    • Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686. (2) (a) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
    • Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686. (2) (a) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
  • 5
    • 0035803051 scopus 로고    scopus 로고
    • An interesting example of internal recycling was reported by Loh where an In0-mediated Barbier-type aldehyde allylation reaction generated a γ-adduct, which rearranged to an α-adduct in an In 3+-catalyzed manner, a Loh, T.-P, Tan, K.-T, Hu, Q.-Y Tetrahedron Lett. 2001, 42, 8705
    • 3+-catalyzed manner. (a) Loh, T.-P.; Tan, K.-T.; Hu, Q.-Y Tetrahedron Lett. 2001, 42, 8705.
  • 7
    • 61349189290 scopus 로고    scopus 로고
    • A conceptually unique but related strategy called cascade catalysis refers to the use of several different catalysts in one-pot procedures to catalyze mechanistically distinct steps of a cascade reaction. The approach presented here is fundamentally different but could, in theory, be used in combination with cascade catalysis
    • A conceptually unique but related strategy called cascade catalysis refers to the use of several different catalysts in one-pot procedures to catalyze mechanistically distinct steps of a cascade reaction. The approach presented here is fundamentally different but could, in theory, be used in combination with cascade catalysis.
  • 8
    • 61349184095 scopus 로고    scopus 로고
    • Comins, D. L.; Joseph, S. P. In Comprehensive Heterocyclic Chemistry, 2nd ed.; McKillop, A., Ed.; Pergamon: Oxford, UK, 1996; 5, ρ 37.
    • (a) Comins, D. L.; Joseph, S. P. In Comprehensive Heterocyclic Chemistry, 2nd ed.; McKillop, A., Ed.; Pergamon: Oxford, UK, 1996; Vol. 5, ρ 37.
  • 13
    • 61349171597 scopus 로고    scopus 로고
    • While this work was in progress, Banik reported an optimized procedure. See: Org. Synth. 2005, 81, 188
    • While this work was in progress, Banik reported an optimized procedure. See: Org. Synth. 2005, 81, 188.
  • 18
    • 61349128795 scopus 로고    scopus 로고
    • 0 or NaOTf, <5% product was detected, even after 24 h.
    • 0 or NaOTf, <5% product was detected, even after 24 h.
  • 20
    • 61349142759 scopus 로고    scopus 로고
    • Aldehydes tested include propionaldehyde, 2-methylpropionaldehyde, cyclohexanecarboxaldehyde, and pivaldehyde
    • Aldehydes tested include propionaldehyde, 2-methylpropionaldehyde, cyclohexanecarboxaldehyde, and pivaldehyde.
  • 21
    • 0002980424 scopus 로고    scopus 로고
    • Authentic samples of m- and p-methoxyphenyl products 1h were used in these experiments. Each of the three isomers (o-, m-, and p-substituted 1h) were treated with 1-8 equiv of CAN in MeCN/water or MeOH/water at temperatures ranging from -12 °C to rt, under an atmosphere of nitrogen, and also in air. All reactions afforded intractible mixtures containing a poor yield of the desired product. For leading references on N-dearylation, see: (a) Sakai, T.; Yan, F.; Uneyama, K. Synlett 1995, 753.
    • Authentic samples of m- and p-methoxyphenyl products 1h were used in these experiments. Each of the three isomers (o-, m-, and p-substituted 1h) were treated with 1-8 equiv of CAN in MeCN/water or MeOH/water at temperatures ranging from -12 °C to rt, under an atmosphere of nitrogen, and also in air. All reactions afforded intractible mixtures containing a poor yield of the desired product. For leading references on N-dearylation, see: (a) Sakai, T.; Yan, F.; Uneyama, K. Synlett 1995, 753.
  • 25
    • 28944434511 scopus 로고    scopus 로고
    • 1H NMR spctroscopy) in these reactions.
    • 1H NMR spctroscopy) in these reactions.
  • 27
    • 0000716787 scopus 로고
    • Trost, B. M, Fleming, I, Eds, Pergamon: Oxford, UK, and references therein
    • (b) Volkmann, R. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol I, p 355 and references therein.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 355
    • Volkmann, R.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.