Diastereoselective Synthesis of Novel and Enantiopure Tetrahy-dropyrano[3,2-c]quinolines

被引：5
|
作者：
Moshapo, Paseka T. [1 ]
Kinfe, Henok H. [1 ]
机构：
[1] Univ Johannesburg, Dept Chem, Auckland Pk, South Africa
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 23期
关键词：
tetrahydropyrano[3; 2-c]quinoline; Friedel-Crafts alkylation; Povarov reaction; glucal; scandium triflate; DIELS-ALDER REACTIONS; STEREOSELECTIVE-SYNTHESIS; ARYL AMINES; PHENANTHROLINE DERIVATIVES; EFFICIENT SYNTHESIS; TETRAHYDROQUINOLINES; CYCLIZATION; THIOCHROMANS; ALDEHYDES; GLYCALS;
D O I：
10.1055/s-0035-1560174
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Diastereoselective synthesis of novel and enantiopure N-alkylated tetrahydropyrano[3,2-c]quinolines is described via intramolecular Friedel-Crafts alkylation using a 1-O-acetylglucosyl derivative as the key intermediate. Unprecedented formation of new glycal derivatives and ,-unsaturated carbaldehyde products is also discussed.
引用
收藏
页码：3673 / 3686
页数：14
相关论文
共 50 条
  • [1] A synthesis of new Pyrrolo[3,2-c]quinolines
    Dudouit, F
    Houssin, R
    Hénichart, JP
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) : 755 - 758
  • [2] Synthesis and reactions of furo[3,2-c]quinolines and furo[3,2-c]coumarins.
    Abd El-Nabi, HA
    El-din, AMN
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2003, 35 (05) : 509 - 514
  • [3] PYRANO[3,2-C]QUINOLINES
    EIDEN, F
    WENDT, R
    ARCHIV DER PHARMAZIE, 1976, 309 (01) : 70 - 72
  • [4] A FACILE SYNTHESIS OF 2,3-DIHYDROSELENOLO[3,2-C]QUINOLINES AND 2,3-DIHYDROTELLUROLO[3,2-C]QUINOLINES
    RAJA, TK
    MUTHUVIJAYAN, G
    REDDY, PA
    LAKSHMANAN, J
    DIVAKAR, R
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1992, 31 (04): : 270 - 272
  • [5] T3P-A Novel Catalyst for Aza-Diels-Alder Reaction: One-Pot Synthesis of Pyrano [3,2-c]quinolines and furano[3,2-c]quinolines
    Prasanna, T. S. R.
    Raju, K. Mohana
    E-JOURNAL OF CHEMISTRY, 2011, 8 : S420 - S424
  • [6] Diastereoselective Synthesis of Carbohydrate Conjugates: Pyrano[3,2-c ]quinolones
    Kumar, Sumit
    Arora, Aditi
    Kumar, Sandeep
    Kumari, Priti
    Singh, Sunil K.
    Singh, Brajendra K.
    SYNTHESIS-STUTTGART, 2024, 56 (07): : 1157 - 1166
  • [7] Synthesis of some indolo[3,2-c]quinolines and [3,2-d]benzazepines.
    Ibrahim, ESI
    HETEROCYCLIC COMMUNICATIONS, 1996, 2 (06) : 525 - 530
  • [8] SYNTHESIS OF NOVEL INDOLO[3,2-c] QUINOLINES; ETHYL 3-CHLORO-9,11-DIMETHOXY INDOLO[3,2-c] QUINOLINE-6-CARBOXYLATE
    Wahyuningsih, Tutik Dwi
    INDONESIAN JOURNAL OF CHEMISTRY, 2005, 5 (03) : 189 - 192
  • [9] SYNTHESIS AND INVITRO ANTIMALARIAL ACTIVITY OF SOME INDOLO[3,2-C]QUINOLINES
    GO, ML
    KOH, HL
    NGIAM, TL
    PHILLIPSON, JD
    KIRBY, GC
    ONEILL, MJ
    WARHURST, DC
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1992, 27 (04) : 391 - 394
  • [10] SYNTHESIS OF SUBSTITUTED 1H-PYRROLO[3,2-C]QUINOLINES
    PARK, KK
    RAPOPORT, H
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (04) : 1031 - 1032
12345