Approaches to combinatorial synthesis of heterocycles: A solid-phase synthesis of 1,4-dihydropyridines

被引：268
|
作者：
Gordeev, MF
Patel, DV
Gordon, EM
机构：
[1] Affymax Research Institute, Santa Clara, CA 95051
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 03期
关键词：
D O I：
10.1021/jo951706s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Immobilized enamino esters 2 derived from amine-functionalized PAL or Rink polystyrene resins react with preformed 2-arylidene beta-keto esters or directly with beta-keto esters and aldehydes to afford, upon trifluoroacetic acid cleavage, 1,4-dihydropyridine (DHP) derivatives in good yields. The mechanism of this transformation on solid support has been studied using C-13 NMR and IR spectroscopies. This new solid-phase synthesis has been applied to the preparation of several bioactive DHPs and is designed to be amenable to the ''split and pool'' protocol for combinatorial library synthesis.
引用
收藏
页码：924 / 928
页数：5
相关论文
共 50 条
  • [1] Approaches to Combinatorial Synthesis of Heterocycles: A Solid-Phase Synthesis of 1,4-Dihydropyridines
    J Org Chem, 3 (924):
  • [2] Progress in Synthesis of 1,4-Dihydropyridines
    Lu, Lingling
    Xu, Hui
    Zhou, Pan
    Yu, Fuchao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (12) : 2858 - 2879
  • [3] NEW SYNTHESIS OF 1,4-DIHYDROPYRIDINES
    CHENNAT, T
    EISNER, U
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (10): : 926 - 929
  • [4] SYNTHESIS OF 1,2-DIHYDROPYRIDINES AND 1,4-DIHYDROPYRIDINES
    FOWLER, FW
    JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (09): : 1321 - &
  • [5] Solid-phase synthesis of 4-aryl-1,4-dihydropyridines via the Hantzsch three component condensation
    Breitenbucher, JG
    Figliozzi, G
    TETRAHEDRON LETTERS, 2000, 41 (22) : 4311 - 4315
  • [6] SYNTHESIS OF 1,4-DIHYDROPYRIDINES BY CYCLOCONDENSATION REACTIONS
    SAUSINS, A
    DUBURS, G
    HETEROCYCLES, 1988, 27 (01) : 269 - 289
  • [7] Synthesis of 1,4-Dihydropyridines and Their Fluorescence Properties
    Sueki, Shunsuke
    Takei, Ryo
    Zaitsu, Yuto
    Abe, Junya
    Fukuda, Akane
    Seto, Keisuke
    Furukawa, Yukio
    Shimizu, Isao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (24) : 5281 - 5301
  • [8] SYNTHESIS OF 1,4-DIHYDROPYRIDINES AND THEIR HYPOTENSIVE ACTIVITY
    SHINDE, DB
    SHINDE, ND
    SHINGARE, MS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1995, 34 (10): : 920 - 922
  • [9] SYNTHESIS OF 1,4-DIHYDROPYRIDINES IN THE CYCLOCONDENSATION REACTIONS
    SAUSINSH, AE
    DUBURS, GY
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1992, (04): : 435 - 467
  • [10] STUDY ON SYNTHESIS AND PROPERTIES OF 1,4-DIHYDROPYRIDINES
    DOMMISSE, R
    INDUSTRIE CHIMIQUE BELGE-BELGISCHE CHEMISCHE INDUSTRIE, 1974, 39 (01): : 55 - 56
12345