Synthesis of N-substituted thiazolidines and dihydrobenzothiazoles

被引:0
|
作者
Katritzky, Alan R. [1 ]
Singh, Sandeep K. [1 ]
He, Hai-Ying [1 ]
机构
[1] Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, United States
关键词
Nucleophilic substitutions;
D O I
10.1055/s-2002-33636
中图分类号
学科分类号
摘要
Ethyl (4R)-3-(1H-1,2,3-benzotriazol-1-ylmethyl)-1,3-thiazolane-4-carboxylate (6) and 1-[1,3-benzothiazol-3(2H)-ylmethyl]-1H-1,2,3-benzotriazole (8) were readily prepared by reactions of L-cysteine ethyl ester hydrochloride and 1-aminothiophenol with benzotriazole and formaldehyde, respectively, Chiral thiazolidine esters 7a-c were obtained by reactions of intermediate 6 with organozinc derivatives. Nucleophilic substitutions of 8 with Grignard reagents gave N-substituted dihydrobenzothiazoles 9a-c.
引用
收藏
页码:1646 / 1648
相关论文
共 50 条
  • [41] SYNTHESIS AND PROPERTIES OF N-SUBSTITUTED AZACALIX[N]ARENES
    TAKEMURA, H
    SHINMYOZU, T
    MIURA, H
    KHAN, IU
    INAZU, T
    JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1994, 19 (1-4): : 193 - 206
  • [42] Synthesis and Properties of N-Substituted Azacalix[n]arenes
    Takemura, H.
    Shinmyozu, T.
    Miura, H.
    Khan, I. U.
    Journal of Inclusion Phenomena and Molecular Recognition in Chemistry, 1994, 195 (1-4):
  • [43] Asymmetric synthesis of N-substituted N-hydroxyureas
    Laczkowski, Krzysztof Z.
    Pakulski, Marcin M.
    Krzeminski, Marek P.
    Jaisankar, Parasuraman
    Zaidlewicz, Marek
    TETRAHEDRON-ASYMMETRY, 2008, 19 (07) : 788 - 795
  • [44] Synthesis and odor characteristics of N-substituted pyrrolyl ketones derived from N-substituted acetylpyrroles and alcohols
    Zhao, Mingqin
    Hu, Jingyi
    Ji, Xiaoming
    Han, Lu
    Li, Mengxiao
    Lai, Miao
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (04) : 596 - 605
  • [45] SYNTHESIS OF SEVERAL N-SUBSTITUTED ACID AMIDES
    SUGASAWA, S
    OHARA, M
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1952, 72 (08): : 1036 - 1038
  • [46] A CONVENIENT SYNTHESIS OF N-SUBSTITUTED BENZOXAZEPINES AND BENZOXAZINES
    SHARMA, I
    AGARWAL, M
    RAY, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1989, 28 (07): : 592 - 594
  • [47] STRATEGY FOR THE SYNTHESIS OF UNSYMMETRICAL N-SUBSTITUTED POLYAZAMACROCYCLES
    GU, KJ
    MERTES, KB
    MERTES, MP
    TETRAHEDRON LETTERS, 1989, 30 (11) : 1323 - 1326
  • [48] SYNTHESIS OF N-SUBSTITUTED DERIVATIVES OF CARNOSINE AND HOMOCARNOSINE
    BAILIN, G
    LUKTON, A
    JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (02): : 684 - &
  • [49] Synthesis and properties of N-substituted saccharin derivatives
    Soubh, L
    Besch, A
    Otto, HH
    PHARMAZIE, 2002, 57 (06): : 384 - 392
  • [50] Synthesis and characterization of N-substituted hydroxyphenyl benzimidazoles
    Dudley, Timothy
    Laurich, Michael
    LaCoursiere, Emmett
    Mukku, Venugopal
    Piro, Nicholas
    Kassel, William
    Boyko, Walter
    Paul, Jared
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252