Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine

被引：39

作者：

Artamonov, Olexiy S. ^{[1
]}

Slobodyanyuk, Evgeniy Y. ^{[2
,3
,4
]}

Shishkin, Oleg V. ^{[5
]}

Komarov, Igor V. ^{[2
,3
,4
]}

Mykhailiuk, Pavel K. ^{[2
,3
,4
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Organ Chem, UA-02660 Kiev 94, Ukraine

[2] Enamine Ltd, UA-01103 Kiev, Ukraine

[3] Dept Chem, UA-01033 Kiev, Ukraine

[4] Kyiv Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine

[5] Natl Acad Sci, Inst Single Crystals, STC, UA-61001 Kharkov, Ukraine

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 02期

关键词：

amines; trifluoromethyl group; cyclopropane; 4-trifluoromethylpiperidine; drug design; ESTROGEN-RECEPTOR LIGANDS; MULTIGRAM SYNTHESIS; DIHYDROBENZOXATHIIN SERAMS; TRIFLUOROMETHYL GROUP; MEDICINAL CHEMISTRY; FLUORINE; CYCLOPROPANES; DERIVATIVES; DESIGN; ROUTE;

D O I：

10.1055/s-0032-1316831

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two isomeric conformationally restricted analogues of 4-trifluoromethylpiperidine were designed. The synthesis was performed in four steps from commercially available N-benzylmaleimide. The key reaction was the [3+2] cycloaddition between trifluoromethyldiazomethane and N-benzylmaleimide.

引用

页码：225 / 230

页数：6

共 63 条

[61] Fluorinated Amino-Derivatives of the Sesquiterpene Lactone, Parthenolide, as 19F NMR Probes in Deuterium-Free Environments [J].

Woods, James R. ;

Mo, Huaping ;

Bieberich, Andrew A. ;

Alavanja, Tanja ;

Colby, David A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (22) :7934-7941

[62] Discovery of 4-aminomethylphenylacetic acids as γ-secretase modulators via a scaffold design approach [J].

Xin, Zhili ;

Peng, Hairuo ;

Zhang, Andrew ;

Talreja, Tina ;

Kumaravel, Gnanasambandam ;

Xu, Lin ;

Rohde, Ellen ;

Jung, Mi-yong ;

Shackett, Melanie N. ;

Kocisko, David ;

Chollate, Sowmya ;

Dunah, Anthone W. ;

Snodgrass-Belt, Pamela A. ;

Arnold, H. Moore ;

Taveras, Arthur G. ;

Rhodes, Kenneth J. ;

Scannevin, Robert H. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (24) :7277-7280

[63] An Efficient and Safe Method for the Multigram Synthesis of trans-2-(Trifluoromethyl)cyclopropylamine [J].

Yarmolchuk, Vladimir S. ;

Bezdudny, Andrii V. ;

Tolmacheva, Nataliya A. ;

Lukin, Oleg ;

Boyko, Alexander N. ;

Chekotylo, Alexey ;

Tolmachev, Andrei A. ;

Mykhailiuk, Pavel K. .

SYNTHESIS-STUTTGART, 2012, 44 (08) :1152-1154

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