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
[1]  
Abele S, 2000, EUR J ORG CHEM, V2000, P1
[2]   ANTIARTHRITIC AND SUPPRESSOR-CELL INDUCING ACTIVITY OF AZASPIRANES - STRUCTURE-FUNCTION-RELATIONSHIPS OF A NOVEL CLASS OF IMMUNOMODULATORY AGENTS [J].
BADGER, AM ;
SCHWARTZ, DA ;
PICKER, DH ;
DORMAN, JW ;
BRADLEY, FC ;
CHEESEMAN, EN ;
DIMARTINO, MJ ;
HANNA, N ;
MIRABELLI, CK .
JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (11) :2963-2970
[3]   Electrophilic aromatic chlorination and haloperoxidation of chloride catalyzed by polyfluorinated alcohols: A new manifestation of template catalysis [J].
Ben-Daniel, R ;
de Visser, SP ;
Shaik, S ;
Neumann, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (40) :12116-12117
[4]   REACTION IN LOW HYDRATED SOLID-LIQUID HETEROGENEOUS MEDIUM - THIIRANES SYNTHESIS FROM EPOXIDES [J].
BOUDA, H ;
BORREDON, ME ;
DELMAS, M ;
GASET, A .
SYNTHETIC COMMUNICATIONS, 1987, 17 (08) :943-951
[5]   SILICA-GEL ASSISTED SYNTHESIS OF THIIRANES [J].
BRIMEYER, MO ;
MEHROTA, A ;
QUICI, S ;
NIGAM, A ;
REGEN, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) :4254-4255
[6]   Sulfonopeptide inhibitors of leukocyte adhesion [J].
Carson, KG ;
Schwender, CF ;
Shroff, HN ;
Cochran, NA ;
Gallant, DL ;
Briskin, MJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (06) :711-714
[7]   An improved preparation of epoxides from carbonyl compounds by using diiodomethane/methyllithium:: synthetic applications [J].
Concellón, JM ;
Cuervo, H ;
Fernández-Fano, R .
TETRAHEDRON, 2001, 57 (43) :8983-8987
[8]  
Cordero FM, 2002, EUR J ORG CHEM, V2002, P1407, DOI 10.1002/1099-0690(200204)2002:8<1407::AID-EJOC1407>3.0.CO
[9]  
2-I
[10]  
COREY EJ, 1965, J ORG CHEM, V30, P1353