Lithium perchlorate-catalyzed regioselective ring-opening of aziridines with potassium thiocyanate

被引:17
作者
Yadav, JS [1 ]
Reddy, BVS [1 ]
Jyothirmai, B [1 ]
Murty, MSR [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
lithium perchlorate; aziridines; potassium thiocyanate; beta-aminothiocyanates;
D O I
10.1016/j.tetlet.2005.06.165
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aziridines react smoothly with potassium thiocyanate in the presence of a catalytic amount of lithium perchlorate in acetonitrile under mild reaction conditions to afford the corresponding beta-aminothiocyanates in high yields and with high regioselectivity. The combination of lithium perchlorate and acetonitrile provides a convenient catalytic medium to perform the reactions under neutral conditions. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6385 / 6387
页数:3
相关论文
共 24 条
[1]   NUCLEOPHILIC OPENING OF CHIRAL BIS(AZIRIDINES) - A ROUTE TO ENANTIOMERICALLY PURE ALPHA-AMINO ALDEHYDES OR ACIDS AND POLYSUBSTITUTED PIPERIDINES [J].
DUREAULT, A ;
TRANCHEPAIN, I ;
DEPEZAY, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5324-5330
[2]   Synthesis of sulfur-containing heterocyclic compounds based on isothiocyanate derivatives of perfluoroolefins (review) [J].
Furin G.G. ;
Zhuzhgov E.L. .
Chemistry of Heterocyclic Compounds, 2002, 38 (2) :129-150
[3]   Lithium perchlorate/diethylether-catalyzed three-component coupling reactions of aldehydes, hydroxylamines and trimethylsilyl cyanide leading to α-cyanohydroxylamines [J].
Heydari, A ;
Larijani, H ;
Emami, J ;
Karami, B .
TETRAHEDRON LETTERS, 2000, 41 (14) :2471-2473
[4]   MICROBIAL OXIDATION OF CHLOROAROMATICS IN THE ENANTIODIVERGENT SYNTHESIS OF PYRROLIZIDINE ALKALOIDS - TRIHYDROXYHELIOTRIDANES [J].
HUDLICKY, T ;
LUNA, H ;
PRICE, JD ;
RULIN, F .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4683-4687
[5]   UNPRECEDENTED REARRANGEMENT REACTION OF 2-AZIRIDINEMETHANOLS WITH LOWER ORDER LITHIUM METHYLCYANOCUPRATE [J].
IBUKA, T ;
NAKAI, K ;
HABASHITA, H ;
FUJII, N ;
GARRIDO, F ;
MANN, A ;
CHOUNAN, Y ;
YAMAMOTO, Y .
TETRAHEDRON LETTERS, 1993, 34 (46) :7421-7424
[6]   LICLO4-CATALYZED NUCLEOPHILIC-ADDITION TO ALPHA-CHIRAL ALDEHYDES, ALDIMINES, AND OXIRANES [J].
IPAKTSCHI, J ;
HEYDARI, A .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (08) :1905-1912
[7]   Enantioselective addition of diethylzinc to aldehydes in the presence of chiral aprotic ligands [J].
Jin, MJ ;
Kim, YM ;
Lee, KS .
TETRAHEDRON LETTERS, 2005, 46 (15) :2695-2696
[8]  
Jin MJ, 2005, B KOREAN CHEM SOC, V26, P215
[9]  
KATRITZKY AR, 1984, COMPREHENSIVE HETERO, V7, P47
[10]   RING-OPENING REACTIONS OF AZIRIDINES WITH ORGANOMETALLICS [J].
KOZIKOWSKI, AP ;
ISHIDA, H ;
ISOBE, K .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) :2788-2790