Hydroacridines XVIII.: Synthesis and NMR spectroscopic investigation of (4aα,8aβ,9aα,10aβ)-tetradecahydroacridine and some of its derivatives

被引：6

作者：

Potmischil, F ^{[1
]}

Vierhapper, FW

Kalchhauser, H

机构：

[1] Univ Bucharest, Dept Organ Chem, RO-70031 Bucharest, Romania

[2] Univ Vienna, Inst Organ Chem, A-1090 Vienna, Austria

来源：

MONATSHEFTE FUR CHEMIE | 1998年 / 129卷 / 05期

关键词：

acridines; tetradecahydro; C-13; NMR; conformational analysis; N-nitrosamines;

D O I：

10.1007/PL00000108

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reductive amination of (R*,R*)-2,2'-methylene-bis-cyclohexanone (1) with methylamine and potassium borohydride affords a mixture of (4a alpha,8a beta,9a alpha,10a beta)- and (4a alpha,8a alpha,9a beta,10a alpha)-tetradecahydro-10-methylacridine (2, 3) in a ratio of approximately 1.3:1 in 57% overall yield. By N-demethylation of 2, via the N-nitrosamine 4 the first synthesis of (4a alpha,8a beta,9a alpha,10a beta)-tetradecahydroacridine (5) could be performed. The relative configurations and conformations of compounds 2-5 as well as the barrier of conformational inversion of 5(Delta G(300)(#), = 55.5 +/- 0.4kJ.mol(-1)) were determined by NMR spectroscopy.

引用

页码：515 / 522

页数：8

共 32 条

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