An improved synthesis of pyridoxine via [2+2+2] cyclization of acetylenes and nitriles

被引：19
作者：
Gutnov, A
Abaev, V
Redkin, D
Fischer, C
Bonrath, W
Heller, B
机构：
[1] Univ Rostock eV, Leibinz Inst Organ Katalyse, D-18055 Rostock, Germany
[2] DSM Nutr Prod Ltd, CH-4303 Kaiseraugst, Switzerland
来源：
SYNLETT | 2005年 / 07期
关键词：
pyridines; alkynes; nitriles; cyclizations; vitamins;
D O I：
10.1055/s-2005-864834
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An improved synthesis of pyridoxine (vitamin B-6) is reported. The key step involves the light-promoted [2+2+2] cyclization of 3,3-bissilyl-di-2-propynyl ethers and acetonitrile in the presence of [cpCo(cod)] (1 mol%) as a catalyst. Convenient oxidation and iodination procedures are elaborated to transfer 3-silyl-pyridines into corresponding 3-hydroxy- and 3-iodo-derivatives.
引用
收藏
页码：1188 / 1190
页数：3
相关论文
共 17 条
  • [1] ORGANOCOBALT COMPOUNDS IN THE SYNTHESIS OF PYRIDINES - AN EXAMPLE OF STRUCTURE-EFFECTIVITY RELATIONSHIPS IN HOMOGENEOUS CATALYSIS
    BONNEMANN, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (04): : 248 - 262
  • [2] TRANSITION-METAL-CATALYZED ALKYNE CYCLIZATIONS - A COBALT-MEDIATED TOTAL SYNTHESIS OF DL-ESTRONE
    FUNK, RL
    VOLLHARDT, KPC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (16) : 5253 - 5261
  • [3] COBALT-CATALYZED CYCLOADDITION OF ALKYNES AND NITRILES TO PYRIDINES - A NEW ROUTE TO PYRIDOXINE (VITAMIN-B6)
    GEIGER, RE
    LALONDE, M
    STOLLER, H
    SCHLEICH, K
    [J]. HELVETICA CHIMICA ACTA, 1984, 67 (05) : 1274 - 1282
  • [4] Grotjahn D. B, 1995, COMPREHENSIVE ORGANO, V12, P741
  • [5] Cobalt(I)-catalyzed asymmetric [2+2+2] cycloaddition of alkynes and nitriles: Synthesis of enantiomerically enriched atropoisomers of 2-arylpyridines
    Gutnov, A
    Heller, B
    Fischer, C
    Drexler, HJ
    Spannenberg, A
    Sundermann, B
    Sundermann, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) : 3795 - 3797
  • [6] Facile and racemization-free conversion of chiral nitriles into pyridine derivatives
    Heller, B
    Sundermann, B
    Fischer, C
    You, JS
    Chen, WQ
    Drexler, HJ
    Knochel, P
    Bonrath, W
    Gutnov, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) : 9221 - 9225
  • [7] Photocatalyzed [2+2+2]-cycloaddition of nitriles with acetylene: An effective method for the synthesis of 2-pyridines under mild conditions
    Heller, B
    Sundermann, B
    Buschmann, H
    Drexler, HJ
    You, JS
    Holzgrabe, U
    Heller, E
    Oehme, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) : 4414 - 4422
  • [8] FIRST COBALT(I)-CATALYZED HETEROCYCLOTRIMERIZATION OF ETHYNE WITH NITRILES TO PYRIDINES IN WATER UNDER MILD CONDITIONS
    HELLER, B
    OEHME, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (02) : 179 - 180
  • [9] The oxidation of the carbon-silicon bond
    Jones, GR
    Landais, Y
    [J]. TETRAHEDRON, 1996, 52 (22) : 7599 - 7662
  • [10] KROLEVETS AA, 1988, J GEN CHEM USSR, V58, P2023
12