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
  • [41] Microwave solvent-free condition synthesis and pharmacological evaluation of pyrano[3,2-c]quinolines
    Nadaraj, Vetrivel
    Selvi, Senniappan Thamarai
    Bai, Helen Pricilla
    Mohan, Sellappan
    Thangadurai, Thangaian Daniel
    MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (10) : 2902 - 2910
  • [42] SYNTHESIS OF FURO[3,2-C]COUMARINES
    AKSANOVA, LA
    SHARKOVA, LM
    KUCHEROV.NF
    ZAGOREVS.VA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1971, (04): : 566 - &
  • [43] SYNTHESIS OF PYRIDO[3,2-C]PYRIDAZINES
    TURCK, A
    BRUMENT, JF
    QUEGUINER, G
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (01) : 101 - 103
  • [44] SYNTHESIS OF FURO[3,2-C]PYRIDINES
    ELOY, F
    DERYCKER.A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (01) : 57 - &
  • [45] Route for the Generation of Trifluoromethyl-Substituted Pyrrplo[3,2-c]quinolines
    Zheng, Danqing
    Liu, Tong
    Liu, Xia
    Fan, Xiaona
    Wu, Jie
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9428 - 9432
  • [46] SYNTHESES OF FURO[3,2-C]COUMARIN, PYRROLO[3,2-C]COUMARIN AND THIENO[3,2-C]COUMARIN
    TRKOVNIK, M
    DJUDJIC, R
    TABAKOVIC, I
    KULES, M
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1982, 14 (1-2) : 21 - 29
  • [47] Stereoselective synthesis of pyrano[3,2-c]- and furano[3,2-c]quinolines:: Samarium diiodide-catalyzed one-pot aza-Diels-Alder reactions
    Zhou, Zhuqing
    Xu, Fan
    Han, Xiaoyan
    Zhou, Jun
    Shen, Qi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (31) : 5265 - 5269
  • [48] A FACILE AND CONVENIENT SYNTHETIC METHOD FOR FLUORINE-CONTAINING DIBENZO[b,h][1,6]NAPHTHYRIDINES, THIOCHROMENO[3,2-c]QUINOLINES, AND CHROMENO[3,2-c]QUINOLINES
    Okada, Etsuji
    Hatakenaka, Mizuki
    Kuratani, Masayuki
    Mori, Takashi
    Ashida, Takuro
    HETEROCYCLES, 2014, 88 (01) : 799 - 806
  • [50] Condition-Dependent Selective Synthesis of Indolo[1,2-c]quinazolines and Indolo[3,2-c]quinolines from and Sulfoxonium Ylides
    Chen, Guang
    Cai, Xinyuan
    Zhang, Xinying
    Fan, Xuesen
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 9815 - 9828