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Volumn 48, Issue 4, 2007, Pages 589-593

Conjugated additions of amines and β-amino alcohols to trifluorocrotonic acid derivatives: synthesis of ψ[NHCH(CF3)]-retro-thiorphan

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; CROTONIC ACID DERIVATIVE; ETHYLAMINE; N TRIFLUOROCROTONOYLOXAZOLIDIN 2 ONE; OXAZOLIDINE DERIVATIVE; RETROTHIORPHAN; TRIFLUOROCROTONIC ACID DERIVATIVE; TRIFLUOROETHYLAMINE; UNCLASSIFIED DRUG;

EID: 33845743839     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.124     Document Type: Article
Times cited : (25)

References (24)
  • 4
    • 33845757016 scopus 로고    scopus 로고
    • Soloshonok V.A. (Ed), ACS Publications Division and Oxford University Press, Washington, DC
    • Sani M., Molteni M., Bruché L., Volonterio A., and Zanda M. In: Soloshonok V.A. (Ed). Fluorine-Containing Synthons (2005), ACS Publications Division and Oxford University Press, Washington, DC 572-592
    • (2005) Fluorine-Containing Synthons , pp. 572-592
    • Sani, M.1    Molteni, M.2    Bruché, L.3    Volonterio, A.4    Zanda, M.5
  • 14
    • 33845795463 scopus 로고    scopus 로고
    • note
    • 3): δ 7.29 (m, 5H), 4.39 (m, 1H), 4.21 (m, 2H), 4.03 (d, J = 13.2 Hz, 1H), 3.85 (d, J = 13.2 Hz, 1H), 3.79 (m, 1H), 3.43 (dd, J = 16.2 and 9.4 Hz, 1H), 3.11 (dd, J = 16.2 and 4.1 Hz, 1H), 2.39 (m, 1H), 0.92 (d, J = 7.1 Hz, 3H), 0.84 (d, J = 6.8 Hz, 3H).
  • 15
    • 0033550292 scopus 로고    scopus 로고
    • note
    • Another possible pathway to 6 could be the fragmentation into ketene 7 and the corresponding deacylated 2-oxazolidinone, followed by reaction with benzylamine.{A figure is presented} The protic acids successfully used in Table 1, entries 1-5,11 could therefore play the role of rapidly quenching the intermediate α-carbonyl carbanion formed by aza-Michael addition, thus suppressing the fragmentation via ketene 7. The formation of ketenes by fragmentation of N-acyl-oxazolidinones has been observed previously: Bravo, P.; Fustero, S.; Guidetti, M.; Volonterio, A.; Zanda, M. J. Org. Chem. 1999, 64, 8731-8735 and references cited therein. Attempts to isolate these hypothetic ketene intermediates by adding external nucleophiles, such as dialkylamines, in the reaction mixture were unsuccessful.
  • 17
    • 33845725891 scopus 로고    scopus 로고
    • note
    • 3): δ 7.33-7.18 (m, 5H), 4.41 (m, 1H), 4.23 (m, 2H), 3.86 (m, 1H), 3.49-3.32 (m, 4H), 3.04 (dd, J = 16.6 and 3.9 Hz, 1H), 2.85 (dd, J = 13.5 and 7.3 Hz, 1H), 2.74 (dd, J = 13.5 and 6.2 Hz, 1H), 2.40 (m, 1H), 1.61 (br s, 1H), 0.91 (d, J = 6.9 Hz, 3H), 0.86 (d, J = 6.9 Hz, 3H).
  • 18
    • 33845740525 scopus 로고    scopus 로고
    • note
    • D -23.3 (c 0.6, methanol).
  • 19
    • 33845790392 scopus 로고    scopus 로고
    • note
    • Compounds 1 are indefinitely stable upon storage at 4 °C (neat). However, the stability is much lower when diastereomers 1 are stored in solution at room temperature, and definitely low when heated in the presence of bases, and in general at pH > 7. This precluded, in our hands, the possibility to isolate diastereopure 1 by crystallization with chiral bases.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.