Reactions of 3-substituted 3-azabicyclo[3.3.1]nonan-9-ones with nitrogen-containing nucleophiles

被引：8

作者：

Moskalenko, A. I. ^{[1
]}

Boev, V. I. ^{[1
]}

机构：

[1] Lipetsk State Pedag Univ, Lipetsk 398020, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 45卷 / 06期

关键词：

Hydrazine Hydrate; Reductive Amination; Anhydrous Calcium Chloride; Sodium Hydrogen Carbonate; Colorless Oily Substance;

D O I：

10.1134/S1070428009060165

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of 3-substituted 3-azabicyclo[3.3.1]nonan-9-ones with hydroxylamine and hydrazine hydrate gave the corresponding oximes, hydrazones, and azines. Reductive amination of the title compounds in the presence of sodium triacetoxyhydridoborate led to the formation of 3-substituted 3-azabicyclo[3.3.1]nonan-9-amines which were converted into the corresponding dihydrochlorides by treatment with dry hydrogen chloride. Treatment of 3-tert-butoxycarbonyl derivatives with HCl under analogous conditions was accompanied by elimination of the tert-butoxycarbonyl group to produce 3-azabicyclo[3.3.1]nonan-9-amine dihydrochlorides.

引用

页码：895 / 899

页数：5

共 50 条

[1] Reactions of 3-substituted 3-azabicyclo[3.3.1]nonan-9-ones with nitrogen-containing nucleophiles
A. I. Moskalenko
V. I. Boev
Russian Journal of Organic Chemistry, 2009, 45 : 895 - 899
[2] REDUCTIONS OF SUBSTITUTED 3,7-DIAZA-7-AZABICYCLO[3.3.1]NONAN-9-ONES AND 3-THIA-7-AZABICYCLO[3.3.1]NONAN-9-ONES WITH SODIUM-BOROHYDRIDE
HALLER, R
ASHAUER, U
ARCHIV DER PHARMAZIE, 1985, 318 (05) : 405 - 410
[3] Synthesis of N-arylmethyl-3-azabicyclo[3.3.1]nonan-9-ones
A. I. Moskalenko
V. I. Boev
Russian Journal of Organic Chemistry, 2009, 45 : 472 - 474
[4] 3-Substituted 3-Azabicyclo[3.3.1]nonan-9-ols and Their Transformations Involving the Hydroxy Group
Moskalenko, A. I.
Boev, V. I.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (10) : 1527 - 1533
[5] Synthesis of N-arylmethyl-3-azabicyclo[3.3.1]nonan-9-ones
Moskalenko, A. I.
Boev, V. I.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (03) : 472 - 474
[6] CONFORMATIONAL AND CONFIGURATIONAL ISOMERS OF SUBSTITUTED 3-OXA-7-AZABICYCLO[3.3.1]NONAN-9-ONES
ASHAUERHOLZGRABE, U
BUSCH, T
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1988, 43 (07): : 873 - 877
[7] SPLITTING OF THE CARBONYL STRETCHING BAND IN THE IR-SPECTRA OF CERTAIN 3-AZABICYCLO[3.3.1]NONAN-9-ONES
BALIAH, V
JEYARAMAN, R
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1978, 16 (12): : 1127 - 1128
[8] SYNTHESIS OF 3-OXA-7-AZABICYCLO[3.3.1]NONAN-9-ONES
BALIAH, V
MANGALAM, G
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1978, 16 (03): : 237 - 238
[9] A complete 1D and 2D NMR studies of variously substituted 3-azabicyclo[3.3.1]nonan-9-ones
Park, Dong Ho
Jeong, Yeon Tae
Parthiban, Paramasivam
JOURNAL OF MOLECULAR STRUCTURE, 2011, 1005 (1-3) : 31 - 44
[10] Reactions of N-substituted 3-azabicyclo[3.3.1]nonan-9-ones with N,N-, N,S-, and N,O-binucleophiles
A. I. Moskalenko
V. I. Boev
Russian Journal of Organic Chemistry, 2009, 45 : 1018 - 1023

← 1 2 3 4 5 →