Last of the gem-Difluorocycloalkanes 2: Synthesis of Fluorinated Cycloheptane Building Blocks

被引:8
作者
Herasymchuk, Maksym [1 ,2 ]
Melnykov, Kostiantyn P. [1 ,2 ]
Yarmoliuk, Dmytro V. [1 ]
Serhiichuk, Dmytro [1 ]
Rotar, Valeriia [1 ,3 ]
Pukhovoi, Timur [1 ,3 ]
Kuchkovska, Yuliya O. [1 ,2 ]
Holovach, Sergey [1 ,4 ]
Volochnyuk, Dmitriy M. [1 ,2 ,4 ]
Ryabukhin, Sergey V. [1 ,2 ]
Grygorenko, Oleksandr O. [1 ,2 ]
机构
[1] Enamine Ltd, Chervonotkatska St 78, UA-020941 Kiev, Ukraine
[2] Taras Shevchenko Natl Univ Kyiv, Volodymyrska St 60, UA-01601 Kiev, Ukraine
[3] Natl Tech Univ Ukraine, Igor Sikorsky Kyiv Polytech Inst, Prospect Peremogy 37, UA-03056 Kiev, Ukraine
[4] Natl Acad Sci Ukraine, Inst Organ Chem, Chervonotkatska St 78, UA-02094 Kiev, Ukraine
关键词
Fluorine; Cycloalkane; Cycloheptane; Deoxofluorination; Building blocks; BETA-KETO-ESTERS; RING-EXPANSION; PHARMACEUTICALS; CHEMISTRY; POLARITY;
D O I
10.1002/ejoc.202001530
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The gem-difluorocycloalkane family was extended to all possible regioisomers of the gem-difluorocycloheptane, monofunctionalized by carboxilic-, amino- or keto- group, that were synthesized on a multigram scale. The preparation of the corresponding building blocks was achieved from readily accessible starting materials either via six-membered ring homologation or deoxofluorination of the appropriate seven-membered cyclic ketones.
引用
收藏
页码:6561 / 6569
页数:9
相关论文
共 43 条
[1]   Synthesis of Functionalized Difluorocyclopropanes: Unique Building Blocks for Drug Discovery [J].
Bychek, Roman M. ;
Levterov, Vadym V. ;
Sadkova, Iryna V. ;
Tolmachev, Andrey A. ;
Mykhailiuk, Pavel K. .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (47) :12291-12297
[2]   Fluoroalkyl-Substituted Cyclopropane Derivatives: Synthesis and Physicochemical Properties [J].
Chernykh, Anton, V ;
Olifir, Oleksandr S. ;
Kuchkovska, Yuliya O. ;
Volochnyuk, Dmitriy M. ;
Yarmolchuk, Vladimir S. ;
Grygorenko, Oleksandr O. .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (19) :12692-12702
[3]   Last of the gem-Difluorocycloalkanes: Synthesis and Characterization of 2,2-Difluorocyclobutyl-Substituted Building Blocks [J].
Chernykh, Anton V. ;
Melnykov, Kostiantyn P. ;
Tolmacheva, Nataliya A. ;
Kondratov, Ivan S. ;
Radchenko, Dmytro S. ;
Daniliuc, Constantin G. ;
Volochnyuk, Dmitriy M. ;
Ryabukhin, Sergey V. ;
Kuchkovska, Yuliya O. ;
Grygorenko, Oleksandr O. .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (13) :8487-8496
[4]   Maraviroc (UK-427,857), a potent, orally bioavailable, and selective small-molecule inhibitor of chemokine receptor CCR5 with broad-spectrum anti-human immunodeficiency virus type 1 activity [J].
Dorr, P ;
Westby, M ;
Dobbs, S ;
Griffin, P ;
Irvine, B ;
Macartney, M ;
Mori, J ;
Rickett, G ;
Smith-Burchnell, C ;
Napier, C ;
Webster, R ;
Armour, D ;
Price, D ;
Stammen, B ;
Wood, A ;
Perros, M .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2005, 49 (11) :4721-4732
[6]   NOVEL FREE-RADICAL RING-EXPANSION REACTIONS [J].
DOWD, P ;
CHOI, SC .
TETRAHEDRON, 1989, 45 (01) :77-90
[7]   Fluorocyclohexanes: synthesis and structure of all-syn-1,2,4,5-tetrafluorocyclohexane [J].
Durie, Alastair J. ;
Slawin, Alexandra M. Z. ;
Lebl, Tomas ;
Kirsch, Peer ;
O'Hagan, David .
CHEMICAL COMMUNICATIONS, 2012, 48 (77) :9643-9645
[8]  
F Armarego W.L., 2013, Purification of Laboratory Chemicals, VSeventh
[9]   Fluorine containing cyclopropanes: synthesis of aryl substituted all-cis 1,2,3-trifluorocyclopropanes, a facially polar motif [J].
Fang, Zeguo ;
Cordes, David B. ;
Slawin, Alexandra M. Z. ;
O'Hagan, David .
CHEMICAL COMMUNICATIONS, 2019, 55 (71) :10539-10542
[10]   Polar alicyclic rings: synthesis and structure of all cis-1,2,3,4-tetrafluorocyclopentane [J].
Fang, Zeguo ;
Al-Maharik, Nawaf ;
Slawin, Alexandra M. Z. ;
Hl, Michael Bu ;
O'Hagan, David .
CHEMICAL COMMUNICATIONS, 2016, 52 (29) :5116-5119