Synthesis of new 2-alkyl-5-arylimino-2,5-dihydroisothiazole derivatives

被引:1
|
作者
Skrastina, I. [1 ]
Baran, A. [1 ]
Muceniece, D. [1 ]
机构
[1] Latvian Inst Organ Synth, LV-1006 Riga, Latvia
关键词
2-alkyl-5-arylimino-2,5-dihydroisothiazoles; 2-substituted N-arylamides of 2-alkylaminobut-2-enethioic acid; enamine-imine tautomerism; oxidative cyclization; UBER ISOTHIAZOLE; BENZOTHIAZOLES; CYTOTOXICITY; CYCLIZATION;
D O I
10.1007/s10593-013-1290-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cyclization of 2-substituted N-arylamides of 3-alkylaminobut-2-enethioic acid gave a series of new 2-alkyl-5-arylimino-2,5-dihydroisothiazole derivatives containing a benzoyl or ester group at position 4. A study was carried out on the course of this reaction in the presence of various oxidizing agents, including halogens, N-bromosuccinimide, hydrogen peroxide. Some of the isothiazoles obtained in this work exhibited cytotoxic activity against both normal and cancer cell lines.
引用
收藏
页码:624 / 635
页数:12
相关论文
共 50 条
  • [1] Synthesis of new 2-alkyl-5-arylimino-2,5-dihydroisothiazole derivatives
    I. Skrastiņa
    A. Baran
    D. Muceniece
    Chemistry of Heterocyclic Compounds, 2013, 49 : 624 - 635
  • [2] Synthesis of 2,5-Dihydroisothiazole Derivatives. 2*. 3-Aryl(Hetaryl)-Substituted 2-Alkyl-5-Arylimino-2,5-Dihydroisothiazoles
    Skrastina, I.
    Baran, A.
    Muceniece, D.
    Popelis, J.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (01) : 87 - 102
  • [3] Synthesis of 2,5-Dihydroisothiazole Derivatives. 2*. 3-Aryl(Hetaryl)-Substituted 2-Alkyl-5-Arylimino-2,5-Dihydroisothiazoles
    I. Skrastiņa
    A. Baran
    D. Muceniece
    J. Popelis
    Chemistry of Heterocyclic Compounds, 2014, 50 : 87 - 102
  • [4] Synthesis of Multifunctionalized 2-Iminothiazolidin-4-ones and Their 2-Arylimino Derivatives
    Le Corre, Laurent
    Lang, Maria Chiara Dasso
    Garbay, Christiane
    Gravier-Pelletier, Christine
    Busca, Patricia
    Etheve-Quelquejeu, Melanie
    Braud, Emmanuelle
    SYNTHESIS-STUTTGART, 2016, 48 (24): : 4569 - 4579
  • [5] Synthesis of 2-aryl-5-alkyl-7-methoxylbenzo[b]furan derivatives
    Xue Fei Yang
    Chinese Chemical Letters, 2007, (04) : 380 - 382
  • [6] Synthesis of 2-aryl-5-alkyl-7-methoxylbenzo[b]furan derivatives
    Yang, Xue Fei
    Kong, Ling Yi
    CHINESE CHEMICAL LETTERS, 2007, 18 (04) : 380 - 382
  • [7] A new synthesis of 3-carboxy-2,5-disubstituted furans and their conversion to 5-vinyl derivatives
    Marshall, JA
    Zou, D
    TETRAHEDRON LETTERS, 2000, 41 (09) : 1347 - 1350
  • [8] Synthesis and Hepatoprotective Properties of 5-Alkyl-substituted Xymedon Derivatives
    Shashyn, M. S.
    Belyaev, G. P.
    Parfenov, A. A.
    Vyshtakalyuk, A. B.
    Semenov, V. E.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2023, 93 (SUPPL 2) : S550 - S555
  • [9] Synthesis and Hepatoprotective Properties of 5-Alkyl-substituted Xymedon Derivatives
    M. S. Shashyn
    G. P. Belyaev
    A. A. Parfenov
    A. B. Vyshtakalyuk
    V. E. Semenov
    Russian Journal of General Chemistry, 2023, 93 : S550 - S555