A novel general route for the preparation of enantiopure imidazolines

被引:82
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
    BEGER, J
    SCHODE, D
    VOGEL, J
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE, 1969, 311 (03): : 408 - &
  • [3] NITROACETAMIDATION OF STYRENES
    BLOOM, AJ
    FLEISCHMANN, M
    MELLOR, JM
    [J]. 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
    BOTTEGHI, C
    SCHIONATO, A
    CHELUCCI, G
    BRUNNER, H
    KURZINGER, A
    OBERMANN, U
    [J]. 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
    Bousquet, P
    Feldman, J
    [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)]
    Cetinkaya, B
    Cetinkaya, E
    Hitchcock, PB
    Lappert, MF
    Ozdemir, I
    [J]. 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
    Çetinkaya, B
    Alici, B
    Özdemir, I
    Bruneau, C
    Dixneuf, PH
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 575 (02) : 187 - 192