Selective formation of a vicinal dinitro derivative via nitrosochlorination of the sesquiterpene lactone achillin

被引:2
作者
Adekenov, SM
Alebastrov, OV
Raldugin, VA
Bagryanskaya, IY
Gatilov, YV
Shakirov, MM
Kulyyasov, AT
Tolstikov, GA
机构
[1] Minist Educ & Sci Republ Kazakhstan, Inst Phytochem, Karaganda 470032, Kazakhstan
[2] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia
基金
俄罗斯基础研究基金会;
关键词
sesquiterpenoids; guaianolides; achillin; nitrosochlorination; nitrocompound; x-ray structure analysis;
D O I
10.1023/A:1012509821962
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Bubbling gaseous nitrosylchloride through a chloroform solution of the guaianolide achillin produces very lowly but selectively 1,10-dihydro-1alpha,10alpha-dinitroachillin. This product rapidly, quantitatively, and irreversibly isomerizes into the dinitrocarboxylic acid with retention of the guaian carbon skeleton upon dissolution in pyridine. The structures of the new compounds were found by x-ray structural analysis.
引用
收藏
页码:228 / 233
页数:6
相关论文
共 13 条
  • [1] ADEKENOV SM, 1987, KHIM PRIR SOEDIN+, P305
  • [2] ALEBASTROV OV, 2000, IZV AKAD NAUK SSSR K
  • [3] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS
    ALLEN, FH
    KENNARD, O
    WATSON, DG
    BRAMMER, L
    ORPEN, AG
    TAYLOR, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12): : S1 - S19
  • [4] Brauer G., 1975, HDB PREPARATIVEN ANO
  • [5] Fieser L.F., 1967, Reagents for Organic Synthesis, V1st
  • [6] THE NITRATION OF PENTAMETHYLPHENOL
    HARTSHORN, MP
    ROBINSON, WT
    VAUGHAN, J
    WHITE, JM
    WHYTE, AR
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1984, 37 (07) : 1489 - 1502
  • [7] KADZYAUKAS PP, 1968, USP KHIM, P1243
  • [8] MAKHMUDOV MK, 1995, KHIM PRIR SOEDIN+, P257
  • [9] NITROSYL CHLORIDE
    MORTON, JR
    WILCOX, HW
    [J]. INORGANIC SYNTHESES, 1953, 4 : 48 - 52
  • [10] OGLOBLIN KA, 1964, ZH OBSHCH KHIM+, V34, P2688