Syntheses based on anabasine.: Preparation and transformations of N-oxides

被引：3

作者：

Musina, L. A.

Shul'ts, E. E.

Krichevskii, L. A.

Adekenov, S. M.

Shakirov, M. M.

Tolstikov, G. A.

机构：

[1] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia

[2] Minist Educ & Sci Republ Kazakhstan, Inst Phytochem, Karaganda 100009, Kazakhstan

来源：

RUSSIAN CHEMICAL BULLETIN | 2006年 / 55卷 / 02期

基金：

俄罗斯基础研究基金会;

关键词：

anabasine; oxidation; anabaseine N-oxide; N-benzoylanabasine pyridine; N-oxide; N-acetyl anabasine pyridine N-oxide; methylanabasine N-oxide; N-benzoylpiperidyl-2-pyridone; N-acetylpiperidyl-2-pyridone; anabasein-3-one;

D O I：

10.1007/s11172-006-0256-5

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The oxidation of N-acetyl- and N-benzoylanabasine with the tert-butyl hydroperoxide (TBHP)-MoCl5 System or MCPBA proceeds selectively at the nitrogen atom of the pyridine ring. The oxidation of N-methylanabasine under similar conditions gives a mixture of stereoisomeric N-oxides at the piperidine nitrogen atom, their ratio depending on the reagent used. The oxidation of anabasine by TBHP-MoCl5 or MCPBA is accompanied by dehydrogenation and results in anabaseine N-oxide. The reactions of anabasine and anabaseine pyridine N-oxides with acetic anhydride were investigated. The substituted 1H-3-pyridin-2-ones were prepared.

引用

页码：331 / 337

页数：7

共 23 条

[1] ANICHKOV EV, 1976, KHIM FARM ZH, P53
[2] ARATYUNYAN LS, 1972, ARM KHIM ZH, P78
[3] ARATYUNYAN LS, 1973, ARM KHIM ZH, P57
[4] ASLANOV KA, 1972, ZH OBSHCH KHIM+, V42, P2293
[5] DOBRENKOV AG, 1988, KHIM PRIR SOEDIN, P129
[6] GODOVIKOV NN, 1974, ZH OBSHCH KHIM+, V44, P687
[7] GOLDFARB YL, 1962, B ACAD SCI USSR DIV, V11
[8] Neuronal nicotinic acetylcholine receptors as targets for drug discovery
Holladay, MW
Dart, MJ
Lynch, JK
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (26) : 4169 - 4194
[9] IBRAGIMOVA GZ, 1984, NAUCH K AKT NYE PROB, P73
[10] KEM RW, 1998, Patent No. 5741802

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