HIGHLY CHEMOSELECTIVE ACYLATION OF SUBSTITUTED AMINOPHENOLS WITH 3-(TRIMETHYLACETYL)-1,3-THIAZOLIDINE-2-THIONE

被引：10
|
作者：
DAI, WM
CHEUNG, YK
TANG, KW
CHOI, PY
CHUNG, SL
机构：
[1] Department of Chemistry, The Hong Kong University of Science and Technology Clear Water Bay, Kowloon
来源：
TETRAHEDRON | 1995年 / 51卷 / 45期
关键词：
D O I：
10.1016/0040-4020(95)00783-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general procedure for chemoselective acylation of substituted aminophenols has been developed. The N-acylated products 7 and 10a-h were prepared by treating me aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione (1) in refluxing THF in 70-100% yield. The eaters 8 and 13d,bj of 3- and 4-amino phenols could be obtained in 70-94% yield by treating with NaH and 1.
引用
收藏
页码：12263 / 12276
页数：14
相关论文
共 50 条
  • [1] REACTION OF 3-(DIMETHYLAMINO)-2H-AZIRINES WITH 1,3-THIAZOLIDINE-2-THIONE
    AMETAMEY, SM
    PREWO, R
    BIERI, JH
    HEIMGARTNER, H
    OBRECHT, JP
    HELVETICA CHIMICA ACTA, 1986, 69 (08) : 2013 - 2025
  • [2] STRUCTURE OF TETRAKIS(1,3-THIAZOLIDINE-2-THIONE)PALLADIUM(II) DICHLORIDE-1,3-THIAZOLIDINE-2-THIONE (1-2)
    KUBIAK, M
    GLOWIAK, T
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1982, 38 (JUL): : 2031 - 2034
  • [3] Synthesis and Crystal Structure of 3-(9-fluorenylmethoxycarbonyl)-1,3-thiazolidine-2-thione
    Li, YZ
    Guo, CX
    Hu, XS
    Du, LP
    Huang, HM
    ACTA CHIMICA SINICA, 1998, 56 (07) : 655 - 661
  • [4] ALKYLATION, ACYLATION, AND CARBAMOYLATION PRODUCTS OF 5-METHYLENE-1,3-THIAZOLIDINE-2-THIONE
    HANEFELD, W
    BERCIN, E
    LIEBIGS ANNALEN DER CHEMIE, 1985, (01): : 58 - 64
  • [5] SYNTHESIS OF 1,3-THIAZOLIDINE-2-THIONE AND (4R)-METHOXYCARBONYL-1,3-THIAZOLIDINE-2-THIONE USING N,N'-THIOCARBONYLDIIMIDAZOLE
    SOAI, K
    ISHIZAKI, M
    HETEROCYCLES, 1984, 22 (12) : 2827 - 2828
  • [6] 3-[4,5-bis(2-cyanoethylsulfanyl)-1,3-dithiol-2-yl]-1,3-thiazolidine-2-thione
    Yang, Wei
    Ren, Zhi-Gang
    Dai, Jie
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O2598 - U1112
  • [7] 1,3-THIAZOLIDINE-2-THIONE - CRYSTAL-STRUCTURE AND COORDINATION CHEMISTRY
    RAPER, ES
    OUGHTRED, RE
    NOWELL, IW
    INORGANICA CHIMICA ACTA-LETTERS, 1983, 77 (03): : L89 - L93
  • [8] VIBRATIONAL ANALYSIS OF 1,3-THIAZOLIDINE-2-THIONE AND ITS SELENIUM ANALOG
    DEVILLANOVA, FA
    DEVI, KRG
    SATHYANARAYANA, DN
    VERANI, G
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1979, 35 (09) : 1083 - 1087
  • [9] A triclinic polymorph of 1,3-thiazolidine-2-thione (2-mercaptothia-zoline)
    Corrêa, RS
    Santana, SA
    Salloum, R
    Silva, RM
    Doriguetto, AC
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2006, 62 (03): : O115 - O117
  • [10] 3,3'-(1-Oxopropane-1,3-diyl)bis(1,3-thiazolidine-2-thione) chlorobenzene hemisolvate
    Franzel, Christine
    Purdy, Andrew
    Butcher, Ray J.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O375 - +
12345