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
  • [31] SYNTHESIS OF NITROGEN HETEROCYCLICS .7. SYNTHESIS OF 2,3-DIHYDROFURO[3,2-C]QUINOLINES
    ARJUNGI, KN
    GOGTE, VN
    TILAK, BD
    INDIAN JOURNAL OF CHEMISTRY, 1969, 7 (10): : 952 - &
  • [32] Synthesis of a novel heterocyclic system:: Oxazolo[3,2-c]pyrimidine
    Bakavoli, M
    Heravi, MM
    Germaninajad, H
    Rahimizadeh, M
    Ghassemzadeh, M
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2006, 181 (02) : 381 - 385
  • [33] NEW SYNTHESIS OF BENZO[H]FURO[3,2-C]QUINOLINES, ISOSTERIC ANALOGS OF BENZO[C]PHENANTHRIDINES
    DUVAL, O
    GOMES, LM
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (01) : 153 - 159
  • [34] Stereoselective Synthesis of Pyrano[3,2-c] and Furano[3,2-c]quinolines: Gadolinium Chloride Catalyzed One-Pot Aza-Diels-Alder Reactions
    Yu, Yong
    Zhou, Jun
    Yao, Zhigang
    Xu, Fan
    Shen, Qi
    HETEROATOM CHEMISTRY, 2010, 21 (05) : 351 - 354
  • [35] Lanthanide chloride catalyzed imino Diels-Alder reaction.: One-pot synthesis of pyrano[3,2-c]- and furo[3,2-c] quinolines
    Ma, Y
    Qian, CT
    Xie, MH
    Sun, J
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17): : 6462 - 6467
  • [36] A CONVENIENT SYNTHESIS OF 3-ARYL-4-OXO-4,5-DIHYDROFURO[3,2-C] QUINOLINES
    RAO, VS
    DARBARWAR, M
    SYNTHETIC COMMUNICATIONS, 1989, 19 (15) : 2713 - 2719
  • [37] Microwave solvent-free condition synthesis and pharmacological evaluation of pyrano[3,2-c]quinolines
    Vetrivel Nadaraj
    Senniappan Thamarai Selvi
    Helen Pricilla Bai
    Sellappan Mohan
    Thangaian Daniel Thangadurai
    Medicinal Chemistry Research, 2012, 21 : 2902 - 2910
  • [38] AN EFFICIENT SYNTHESIS OF 2,5-DIOXO-5,6-DIHYDROPYRANO[3,2-C]-QUINOLINES
    GUPTA, MCLN
    RAO, VS
    DARBARWAR, M
    SYNTHETIC COMMUNICATIONS, 1990, 20 (14) : 2103 - 2111
  • [39] Convenient synthesis of pyrano[3,2-c]quinolines and indeno[2,1-c] quinolines by imino Diels-Alder reactions
    Babu, G
    Perumal, PT
    TETRAHEDRON LETTERS, 1998, 39 (20) : 3225 - 3228
  • [40] SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 4,5-DIHYDRO-4-OXOTHIENO[3,2-C]QUINOLINES
    JAYASHREE, A
    MALLESHWAR, D
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 287 - ORGN
12345