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

[1] Hydroacridines XXV [1]. First Synthesis of (4aα,8aα,9aβ,10aβ)-Tetradecahydroacridine and New Syntheses of (4aα,8aα,9aα,10aβ)- and (4aα,8aβ,9aα,10aβ)-Tetradecahydroacridine
Francisc Potmischil
Joachim Buddrus
Jörg Lambert
Monatshefte für Chemie / Chemical Monthly, 2006, 137 : 1551 - 1555
[2] Hydroacridines XXV.: First synthesis of (4aα,8aα,9aβ,10aβ)-tetradecahydroacridine and new syntheses of (4aα,8aα,9aα,10aβ)- and (4aα,8aβ,9aα,10aβ)-tetradecahydroacridine
Potmischil, Francisc
Buddrus, Joachim
Lambert, Joerg
MONATSHEFTE FUR CHEMIE, 2006, 137 (12): : 1551 - 1555
[3] Hydroacridines XXI [1]. 13C NMR spectroscopic investigation of the stereoselectivities of quaternizations of N-alkyl derivatives of (4aα,8aβ,9aβ,10aα)- and (4aα,8aα,9aβ,10aα)-tetradecahydroacridine
Potmischil F.
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Buddrus J.
Gheorghiu M.D.
Monatshefte fur Chemie, 2000, 131 (04): : 345 - 352
[4] Hydroacridines .16. Steric effect in the polarographic reduction of N-epimeric amine oxides derived from (4a alpha,8a beta,9a beta,10a alpha)- and (4a alpha,8a alpha,9a beta,10a alpha)-tetradecahydro-10-methylacridine
Spataru, N
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Potmischil, F
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (11): : 2453 - 2457
[5] An efficient synthesis of tricyclic compounds, (+/-)-(4aβ,8aβ,10aα)-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydro-1,1,4a-trimethyl-2-oxophenanthrene-8a-carboxylic acid, its methyl ester, and (+/-)-(4aβ,8aβ,10aα)-3,4,4a,6,7,8,8a,9,10,10a-decahydro-8a-hydroxymethyl-1,1,4a-trimethylphenanthren-2(1H)-one
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ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2005, 37 (06) : 546 - 550
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ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2011, 67 : O294 - O296
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SHERWOOD, BE
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (02): : 183 - 185
[8] SYNTHESIS OF 2,6-DIMETHYL-1,4,4A,5,8,8A,9A,10A-OCTAHYDRO-9,10-ANTHRAQUINONE AND ITS 2,7-DIMETHYL ISOMER
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FOX, BW
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ZHANG, XG
JOURNAL OF CHEMICAL RESEARCH-S, 1994, (06): : 220 - 221
[9] SYNTHESIS OF CIS-1,2,3,4,4A,5,8,8A-OCTAHYDRONAPHTHALENE AND OF CIS-TRANSOID-CIS-1,4,4A,5,8,8A,9,9A,10,10A-DECAHYDROANTHRACENE
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ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 : 303 - 307

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