Unexpected regiochemistry in [3+2] cycloaddition reaction of azomethine ylides of indenoquinoxalinone series to arylidene malononitriles

被引：14
作者：
Barkov, Alexey Yu [1 ]
Zimnitskiy, Nikolay S. [1 ]
Kutyashev, Igor B. [1 ]
Korotaev, Vladislav Yu [1 ]
Sosnovskikh, Vyacheslav Ya [1 ]
机构：
[1] Ural Fed Univ, Inst Nat Sci & Math, 51 Lenina Ave, Ekaterinburg 620000, Russia
来源：
CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2018年 / 54卷 / 01期
关键词：
arylidene malononitriles; indenoquinoxalinones; spiropyrrolidines; spiropyrrolizidines; stabilized azomethine ylides; 1,3-dipolar cycloaddition; STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; IONIC LIQUID; SPIRO-PYRROLIDINE; MULTICOMPONENT; DERIVATIVES; HETEROCYCLES; PYRROLIZIDINES; INHIBITORS; EFFICIENT; NINHYDRIN;
D O I：
10.1007/s10593-018-2228-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3-Dipolar cycloaddition of azomethine ylides generated in situ from proline and indenoquinoxalinones occurred at the double bond of arylidene malononitriles upon heating in isopropanol, leading to the respective spirocyclic adducts with cis orientation of the aryl substituent and the quinoxaline moiety. The regioselectivity of this process depended on the electron donor-acceptor properties of substituents in the aromatic ring of the dipolarophile molecule. Analogous reaction involving azomethine ylide derived from sarcosine produced adducts with a trans relationship of the most sterically demanding substituents.
引用
收藏
页码：43 / 50
页数：8
相关论文
共 36 条
[21]   Expeditious Construction of Spiro-Pyrrolidines by an Autocatalytic One-Pot, Five-Component, 1,3-Dipolar Cycloaddition of in situ Generated Azomethine Ylides and Olefinic Dipolarophiles [J].
Li, Ming ;
Gong, Fu-Meng ;
Wen, Li-Rong ;
Li, Zhao-Rui .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (19) :3482-3490
[22]   Reactions of 2-aryl-1,1-dicyanoethenes with L-proline and aldehydes [J].
Nosachev, S. B. ;
Poddubnyi, O. Yu. ;
Velikorodov, A. V. ;
Tyrkov, A. G. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (05) :674-677
[23]  
Nosachev S. B., 2009, RUSS J ORG CHEM+, V45, p[624, 637]
[24]   Diversity-oriented synthesis: producing chemical tools for dissecting biology [J].
O'Connor, Cornelius J. ;
Beckmann, Henning S. G. ;
Spring, David R. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (12) :4444-4456
[25]   Synthesis of new spirooxindolopyrrolidines via three-component reaction of isatins, α-amino acids, and (E)-3-aryl-2-cyanoacrylamides or (E)-3-aryl-2-(4-arylthiazol-2-yl) acrylonitriles [J].
Pavlovska, Tetyana L. ;
Lipson, Victoria V. ;
Shishkina, Svetlana V. ;
Musatov, Vladimir I. ;
Nichaenko, Julia A. ;
Dotsenko, Victor V. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (04) :460-467
[26]   Regio- and stereoselective synthesis of spirooxindole 1′-nitro pyrrolizidines with five concurrent stereocenters under aqueous medium and their bioprospection using the zebrafish (Danio rerio) embryo model [J].
Puerto Galvis, Carlos E. ;
Kouznetsov, Vladimir V. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (42) :7372-7386
[27]   Multi-component, 1,3-dipolar cycloaddition reactions for the chemo-, regio- and stereoselective synthesis of novel hybrid spiroheterocycles in ionic liquid [J].
Rajesh, Stephen Michael ;
Bala, Balasubramainan Devi ;
Perumal, Subbu .
TETRAHEDRON LETTERS, 2012, 53 (40) :5367-5371
[28]   Identification and Characterization of a Novel Class of c-Jun N-terminal Kinase Inhibitors [J].
Schepetkin, Igor A. ;
Kirpotina, Liliya N. ;
Khlebnikov, Andrei I. ;
Hanks, Tracey S. ;
Kochetkova, Irina ;
Pascual, David W. ;
Jutila, Mark A. ;
Quinn, Mark T. .
MOLECULAR PHARMACOLOGY, 2012, 81 (06) :832-845
[29]   A short history of SHELX [J].
Sheldrick, George M. .
ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES, 2008, 64 :112-122
[30]   An Efficient One-pot Three-component Process for Synthesis of Perfluoroalkylated Quinolizines [J].
Shen, Dandan ;
Xu, Yanjie ;
He, Dong ;
Han, Jing ;
Chen, Jie ;
Deng, Hongmei ;
Shao, Min ;
Zhang, Hui ;
Cao, Weiguo .
CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (05) :524-532
1234