Facile synthesis of 1,1-disubstituted taurines

被引:43
作者
Huang, JX [1 ]
Du, DM [1 ]
Xu, JX [1 ]
机构
[1] Peking Univ, Coll Chem & Mol Engn, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
来源
SYNTHESIS-STUTTGART | 2006年 / 02期
关键词
amino acid; aminoalkanesulfonic acid; epoxide; episulfide; ketone; synthesis; taurine;
D O I
10.1055/s-2005-924767
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of 1,1-disubstituted taurines was synthesized expeditiously from ketones via the Corey-Chaykovsky epoxidation with dimethylsulfonium methylide, episulfidation with potassium sulfocyanate, ring-opening reaction with ammonia in the presence of,silver nitrate, followed by treatment with hydrogen Sulfide and oxidation with performic acid.
引用
收藏
页码:315 / 319
页数:5
相关论文
共 30 条
  • [11] Increased stability of peptidesulfonamide peptidomimetics towards protease catalyzed degradation
    de Bont, DBA
    Sliedregt-Bol, KM
    Hofmeyer, LJF
    Liskamp, RMJ
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (06) : 1043 - 1047
  • [12] SIMPLE, INEXPENSIVE SYNTHESIS OF OXIRANES FROM CARBONYL-COMPOUNDS - GENERATION OF SULFONIUM YLIDES FROM THE TERNARY-SYSTEM METHANOL SULFURIC-ACID DIMETHYL SULFIDE
    FORRESTER, J
    JONES, RVH
    PRESTON, PN
    SIMPSON, ESC
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (17): : 1937 - 1937
  • [13] HEALTH RL, 1947, J CHEM SOC, P1481
  • [14] An expeditious synthesis of 1-substituted and cyclic taurines
    Huang, JX
    Wang, F
    Du, DM
    Xu, JX
    [J]. SYNTHESIS-STUTTGART, 2005, (13): : 2122 - 2128
  • [15] PHYSIOLOGICAL ACTIONS OF TAURINE
    HUXTABLE, RJ
    [J]. PHYSIOLOGICAL REVIEWS, 1992, 72 (01) : 101 - 163
  • [16] Juaristi E, 1999, CURR MED CHEM, V6, P983
  • [17] EFFECTS OF AMINOCYCLOALKANESULFONIC ACID ANALOGS OF TAURINE ON ATP-DEPENDENT CALCIUM-ION UPTAKE AND PROTEIN-PHOSPHORYLATION
    LIEBOWITZ, SM
    LOMBARDINI, JB
    ALLEN, CI
    [J]. BIOCHEMICAL PHARMACOLOGY, 1988, 37 (07) : 1303 - 1309
  • [18] An improved and easy method for the preparation of 2,2-disubstituted 1-nitroalkenes
    Lin, WW
    Jang, YJ
    Wang, Y
    Liu, JT
    Hu, SR
    Wang, LY
    Yao, CF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (06) : 1984 - 1991
  • [19] IMPROVED SYNTHESIS OF AMINOETHANETHIOLS
    LUHOWY, R
    MENEGHIN.F
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (13) : 2405 - 2407
  • [20] MOUSSA GEM, 1980, INDIAN J CHEM B, V19, P798