Facile Synthesis of Novel Hexahydroimidazo[1,2-a]pyridine Derivatives by One-Pot, Multicomponent Reaction under Ambient Conditions

被引：15
作者：
Tan, Hongbo [1 ,2 ]
Wang, Yinfeng [1 ,2 ]
机构：
[1] Chongqing Univ Arts & Sci, Natl & Local Joint Engn Res Ctr Targeted & Innova, Coll Pharm,Chongqing Engn Lab Targeted & Innovat, Chongqing Key Lab Kinase Modulators Innovat Med,C, Chongqing 402160, Peoples R China
[2] Chongqing Univ Arts & Sci, IATTI, Chongqing 402160, Peoples R China
来源：
ACS COMBINATORIAL SCIENCE | 2020年 / 22卷 / 09期
关键词：
mild conditions; multiple bond formation; trans-selectivity; one-pot protocol; multicomponent; BEARING BRIDGEHEAD NITROGEN; NATURAL-PRODUCT SYNTHESIS; HETEROCYCLES; 3-COMPONENT; INHIBITORS; DISCOVERY; DESIGN; CORE;
D O I：
10.1021/acscombsci.0c00105
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient one-pot multicomponent reaction for the synthesis of novel tetrasubstituted hexahydroimidazo[1,2-a]pyridines starting from readily available cinnamaldehydes, ethylenediamines, and 1,3-dicarbonyl compounds catalyzed by AcOH is described. Two new cycles and four new bonds are constructed with all reactants being efficiently utilized in this transformation. The products could be obtained in 1-3 h under ambient conditions exclusively as a single isomer (trans). Single-crystal X-ray analysis confirmed the trans derivative as the only isomer.
引用
收藏
页码：468 / 474
页数：7
相关论文
共 41 条
[1]   Microwave-assisted reaction between 2-aminobenzoic acids, 2-hydroxybenzaldehydes, and arylboronic acids: a one-pot three-component synthesis of bridgehead bicyclo[4.4.0]boron heterocycles [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2012, 68 (16) :3377-3383
[2]   Metal-Free Multicomponent Syntheses of Pyridines [J].
Allais, Christophe ;
Grassot, Jean-Marie ;
Rodriguez, Jean ;
Constantieux, Thierry .
CHEMICAL REVIEWS, 2014, 114 (21) :10829-10868
[3]   Heteropolyacid-Containing Ionic Liquid-Catalyzed Multicomponent Synthesis of Bridgehead Nitrogen Heterocycles: Mechanisms and Mitochondrial Staining [J].
Alvim, Haline G. O. ;
Correa, Jose R. ;
Assumpcao, Jose A. F. ;
da Silva, Wender A. ;
Rodrigues, Marcelo O. ;
de Macedo, Julio L. ;
Fioramonte, Mariana ;
Gozzo, Fabio C. ;
Gatto, Claudia C. ;
Neto, Brenno A. D. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07) :4044-4053
[4]   Employing Arynes in Diels-Alder Reactions and Transition-Metal-Free Multicomponent Coupling and Arylation Reactions [J].
Bhojgude, Sachin Suresh ;
Bhunia, Anup ;
Biju, Akkattu T. .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) :1658-1670
[5]  
Bourgault JP, 2014, ORG BIOMOL CHEM, V12, P8125, DOI [10.1039/C4OB01148A, 10.1039/c4ob01148a]
[6]   Recent developments in asymmetric multicomponent reactions [J].
de Graaff, Corien ;
Ruijter, Eelco ;
Orru, Romano V. A. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3969-4009
[7]   One-pot, multi-component synthesis and structure-activity relationships of peptoid-based histone deacetylase (HDAC) inhibitors targeting malaria parasites [J].
Diedrich, Daniela ;
Stenzel, Katharina ;
Hesping, Eva ;
Antonova-Koch, Yevgeniya ;
Gebru, Tamirat ;
Duffy, Sandra ;
Fisher, Gillian ;
Schoeler, Andrea ;
Meister, Stephan ;
Kurz, Thomas ;
Avery, Vicky M. ;
Winzeler, Elizabeth A. ;
Held, Jana ;
Andrews, Katherine T. ;
Hansen, Finn K. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 158 :801-813
[8]   Convenient Synthesis of Novel Nitrogen Bridgehead Heterocycles Utilizing 3-Mercapto-6H-[1,2,4,5]oxatriazino[3,2-a]isoindol-6-one as a New Synthon [J].
El Azab, Islam H. ;
Elkanzi, Nadia A. A. ;
Gobouri, Adil A. ;
Altalhi, Tariq A. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (01) :60-72
[9]   Multicomponent Hetero-[4+2] Cycloaddition/Allylboration Reaction: From Natural Product Synthesis to Drug Discovery [J].
Hall, Dennis G. ;
Rybak, Taras ;
Verdelet, Tristan .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (11) :2489-2500
[10]   Facile Multicomponent Polymerizations toward Unconventional Luminescent Polymers with Readily Openable Small Heterocycles [J].
Han, Ting ;
Deng, Haiqin ;
Qiu, Zijie ;
Zhao, Zheng ;
Zhang, Haoke ;
Zou, Hang ;
Leung, Nelson L. C. ;
Shan, Guogang ;
Elsegood, Mark R. J. ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (16) :5588-5598
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