A novel general route for the preparation of enantiopure imidazolines

被引:83
作者
Boland, NA
Casey, M [1 ]
Hynes, SJ
Matthews, JW
Smyth, MP
机构
[1] Natl Univ Ireland Univ Coll Dublin, Dept Chem, Dublin 4, Ireland
[2] Natl Univ Ireland Univ Coll Dublin, Conway Inst Biomol & Biomed Res, Dublin 4, Ireland
关键词
D O I
10.1021/jo0111006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel procedure for the preparation of enantiopure 1,4-disubstituted 2-imidazolines is reported. Enantiopure beta-amino alcohols are converted into N-hydroxyethylamides, which are reacted with excess thionyl chloride, or with thionyl chloride followed by phosphorus pentachloride to yield N-chloroethylimidoyl chlorides. These intermediates are treated with amines and anilines to produce N-chloro-ethylamidines, which are converted into imidazolines upon workup with aqueous hydroxide. The method is simple and efficient and has been used to prepare a wide variety of enantiopure imidazolines, in a modular fashion, from readily available amino alcohols.
引用
收藏
页码:3919 / 3922
页数:4
相关论文
共 52 条
[1]  
Bastero A, 2001, EUR J INORG CHEM, P3009
[2]   3-COMPONENT REACTIONS .2. NUCLEOPHILIC SUBSTITUTIONS ON N-(BETA-HALOALKYL)IMIDE HALIDES . SYNTHESIS OF DELTA2-OXAZOLINES, DELTA2-THIAZOLINES AND DELTA2-IMIDAZOLINES [J].
BEGER, J ;
SCHODE, D ;
VOGEL, J .
JOURNAL FUR PRAKTISCHE CHEMIE, 1969, 311 (03) :408-&
[3]   NITROACETAMIDATION OF STYRENES [J].
BLOOM, AJ ;
FLEISCHMANN, M ;
MELLOR, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (10) :2357-2362
[4]  
BOHME H, 1978, TETRAHEDRON LETT, P1429
[5]  
BORISOVA EY, 1975, Patent No. 466231
[6]   ASYMMETRIC CATALYSIS .46. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2 AND OPTICALLY-ACTIVE NITROGEN LIGANDS [J].
BOTTEGHI, C ;
SCHIONATO, A ;
CHELUCCI, G ;
BRUNNER, H ;
KURZINGER, A ;
OBERMANN, U .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 370 (1-3) :17-31
[7]   Drugs acting on imidazoline receptors - A review of their pharmacology, their use in blood pressure control and their potential interest in cardioprotection [J].
Bousquet, P ;
Feldman, J .
DRUGS, 1999, 58 (05) :799-812
[8]  
Busacca C. A., 2001, U.S. Patent, Patent No. [US6316620, 6316620, 6,316,620]
[9]   Synthesis and characterisation of 1-alkyl-2-imidazoline complexes of noble metals; Crystal structure of trans[PtCl2{N=C(H)N(Et)CH2CH2}(PEt3)] [J].
Cetinkaya, B ;
Cetinkaya, E ;
Hitchcock, PB ;
Lappert, MF ;
Ozdemir, I .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (08) :1359-1362
[10]   2-imidazoline and 1,4,5,6-tetrahydropyrimidine-ruthenium(II) complexes and catalytic synthesis of furan [J].
Çetinkaya, B ;
Alici, B ;
Özdemir, I ;
Bruneau, C ;
Dixneuf, PH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 575 (02) :187-192