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

来源：

CHEMISTRY OF NATURAL COMPOUNDS | 2001年 / 37卷 / 03期

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

页码：228 / 233

页数：6

共 6 条

[1] Selective Formation of a Vicinal Dinitro Derivative via Nitrosochlorination of the Sesquiterpene Lactone Achillin
S. M. Adekenov
O. V. Alebastrov
V. A. Raldugin
I. Yu. Bagryanskaya
Yu. V. Gatilov
M. M. Shakirov
A. T. Kulyyasov
G. A. Tolstikov
Chemistry of Natural Compounds, 2001, 37 : 228 - 233
[2] Synthesis and crystal structure of new dinitro derivatives of sesquiterpene lactone achillin
Mynzhasarovich, AS
Bagdatovna, RB
Tabylovich, KA
Zareen, S
Choudhary, MI
Atta-ur-Rahman
HETEROCYCLES, 2003, 60 (05) : 1053 - 1063
[3] AN UNEXPECTED SELECTIVE FORMATION OF A DELTA-LACTONE IN THE OZONOLYSIS OF A SANTONIN DERIVATIVE - NEIGHBORING PARTICIPATION OF A METHOXYCARBONYL GROUP
WATANABE, M
HARADA, N
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22): : 7372 - 7374
[4] Direct lactone formation by using hypervalent Iodine(III) reagents with KBr via selective C-H abstraction protocol
Dohi, Toshifumi
Takenaga, Naoko
Goto, Akihiro
Maruyama, Akinobu
Kita, Yasuyuki
ORGANIC LETTERS, 2007, 9 (16) : 3129 - 3132
[5] SELECTIVE FORMATION OF A 6-MEMBERED LACTONE AND A C-9-CARBOXYLIC ACID-DERIVATIVE FROM BUTADIENE AND CARBON-DIOXIDE CATALYZED BY PALLADIUM
INOUE, Y
OHASHI, R
TOYOFUKU, M
HASHIMOTO, H
NIPPON KAGAKU KAISHI, 1985, (03) : 533 - 536
[6] Unexpected and selective formation of an (e,e,e,e)-tetrakis-[60]fullerene derivative via electrolytic retro-cyclopropanation of a D2h-hexakis-[60]fullerene adduct
Ortiz, Angy L.
Echegoyen, Luis
JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (05) : 1362 - 1364

← 1 →