Synthesis of 6,6-disubstituted tetrahydrothiopheno [3,4-c] isoxazolines from beta-nitroenones

被引：5
|
作者：
Ahrach, M [1 ]
Schneider, R [1 ]
Gerardin, P [1 ]
Loubinoux, B [1 ]
机构：
[1] UNIV NANCY 1,FAC SCI,LAB CHIM ORGAN MICROBIOL,LERMAB,F-54506 VANDOEUVRE NANCY,FRANCE
来源：
SYNTHETIC COMMUNICATIONS | 1997年 / 27卷 / 11期
关键词：
D O I：
10.1080/00397919708006787
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
beta-Nitrosulfides 2, formed by Michael addition of prop-2-en-1-thiol to beta-nitroenones 1 in the presence of a catalytic amount of triethylamine, undergo either Intramolecular Nitrile Oxide Cycloadditions (INOC) or Intramolecular Silylnitronate Cycloadditions (ISOC) to functionalized 6,6-disubstituted tetrahydrothiopheno [3,4-c] isoxazolines 3 and 4. The stereoselectivity, poor by the INOC reactions starting from acyclic beta-nitroenones, is markedly increased with the ISOC procedure.
引用
收藏
页码：1865 / 1876
页数：12
相关论文
共 50 条
  • [21] Synthesis and neurotropic activity of 6,8-diamino derivatives of pyrano[3,4-c]pyridines
    E. G. Paronikyan
    Sh. Sh. Dashyan
    I. A. Dzhagatspanyan
    R. G. Paronikyan
    I. M. Nazaryan
    A. G. Akopyan
    N. S. Minasyan
    A. G. Ayvazyan
    R. A. Tamazyan
    E. V. Babaev
    Russian Journal of Bioorganic Chemistry, 2016, 42 : 215 - 223
  • [22] Synthesis and neurotropic activity of 6,8-diamino derivatives of pyrano[3,4-c]pyridines
    Paronikyan, E. G.
    Dashyan, Sh. Sh
    Dzhagatspanyan, I. A.
    Paronikyan, R. G.
    Nazaryan, I. M.
    Akopyan, A. G.
    Minasyan, N. S.
    Ayvazyan, A. G.
    Tamazyan, R. A.
    Babaev, E. V.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2016, 42 (02) : 215 - 223
  • [23] HETEROCYCLES FROM LEVULINIC ACID .6. FORMATION OF PYRROLO(3,4-C)PYRAZOLES
    WESTPHAL, G
    JOURNAL FUR PRAKTISCHE CHEMIE, 1969, 311 (03): : 379 - &
  • [24] A CONVENIENT SYNTHESIS OF 6-AMINO-1-BETA-D-RIBOFURANOSYLPYRAZOLO[3,4-D]PYRIMIDIN-4-ONE AND RELATED 4,6-DISUBSTITUTED PYRAZOLOPYRIMIDINE NUCLEOSIDES
    COTTAM, HB
    REVANKAR, GR
    ROBINS, RK
    NUCLEIC ACIDS RESEARCH, 1983, 11 (03) : 871 - 882
  • [25] New Efficient Synthesis of 6-Aminopyrano[3,4-c]pyridines via Smiles Type Rearrangement
    Sirakanyan, S. N.
    Kartsev, V. G.
    Hakobyan, E. K.
    Hovakimyan, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (04) : 569 - 572
  • [26] New efficient synthesis of 6-aminopyrano[3,4-c]pyridines via Smiles type rearrangement
    S. N. Sirakanyan
    V. G. Kartsev
    E. K. Hakobyan
    A. A. Hovakimyan
    Russian Journal of Organic Chemistry, 2017, 53 : 569 - 572
  • [27] One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)
    Lu, Xin-Mou
    Li, Jian
    Cai, Zhong-Jian
    Wang, Rong
    Wang, Shun-Yi
    Ji, Shun-Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (46) : 9471 - 9477
  • [28] Methylheteroaromatic carbonitriles as building blocks for synthesis of condensed heteroaromatics:: Novel syntheses of [1]benzo[2,3]pyrano[3,4-c]pyridines, naphtho[2′,1′:5,6]pyrano[3,4-c]pyridines, pyrido[3,4-c]quinolines and other new condensed pyridines
    Al-Omran, F
    Abdel-Khalik, MM
    Abou El-khair, A
    Elnagdi, MH
    JOURNAL OF CHEMICAL RESEARCH-S, 1998, (06): : 294 - +
  • [29] SYNTHESIS OF 6-OXO-2,6-DIHYDRO-4H-FURO[3,4-C]PYRAZOLES AND 6-OXO-4H,6H-FURO[3,4-C] [1,2]OXAZOLES FROM 2-ALKYNYL ACETOACETATES
    GARANTI, L
    SALA, A
    ZECCHI, G
    SYNTHESIS-STUTTGART, 1975, (10): : 666 - 669
  • [30] Direct Synthesis of Pyrrolo[3,4-c]quinolines from the Domino Reaction of Tosylmethyl Isocyanides and Aminochalcones
    Hu, Zhongyan
    Li, Yifei
    Pan, Ling
    Xu, Xianxiu
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 2974 - 2978
12345