Synthesis and Application of Novel Magnetic Glycoluril Tetrakis(Methylene Phosphorous Acid) as a Nano Biological Catalyst for the Preparation of Nicotinonitriles via a Cooperative Vinylogous Anomeric-Based Oxidation

被引：11
作者：
Danishyar, Bashirullah [1 ]
Sepehrmansourie, Hassan [1 ]
Zarei, Mahmoud [1 ]
Zolfigol, Mohammad Ali [1 ]
As'Habi, Mohammad Ali [2 ]
Gu, Yanlong [3 ]
机构：
[1] Bu Ali Sina Univ, Fac Chem, Dept Organ Chem, Hamadan 6517838683, Hamadan, Iran
[2] Shahid Beheshti Univ, Med Plant & Drugs Res Inst, Dept Phytochem, Tehran, Iran
[3] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Wuhan, Peoples R China
来源：
POLYCYCLIC AROMATIC COMPOUNDS | 2023年 / 43卷 / 08期
基金：
美国国家科学基金会;
关键词：
Anomeric effect; anomeric-based oxidation; biological catalyst; diphenyl nicotinonitrile; Fe3O4@GTMPA; Glycoluril tetrakis(methylene phosphorous acid); nano-magnetic catalyst; SULFONIC-ACID TAGS; PYRIDINE-DERIVATIVES; CHEMISTRY; ENAMINES; INDOLES;
D O I：
10.1080/10406638.2022.2126506
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we synthesized biological magnetic glycoluril tetrakis(methylene phosphorous acid) as a new heterogeneous nano-catalyst. The magnetic nano-catalyst Fe3O4@GTMPA was used for the synthesis of diphenyl nicotinonitrile derivatives by multi-component reaction of wide spread aldehydes, acetophenones, ammonium acetate, and 3-(1H-indol-3-yl)-3-oxopropanenitrile in the solvent-free conditions at 110 degrees C. The final step of reaction mechanism was preceded via a cooperative vinylogous anomeric-based oxidation (CVABO) as green and convenient approach.
引用
收藏
页码：6837 / 6857
页数：21
相关论文
共 51 条
[1]   Synthesis and application of melamine-based nano catalyst with phosphonic acid tags in the synthesis of (3′-indolyl)pyrazolo[3,4-b] pyridines via vinylogous anomeric based oxidation [J].
Afsar, Javad ;
Zolfigol, Mohammad Ali ;
Khazaei, Ardeshir ;
Zarei, Mahmoud ;
Gu, Yanlong ;
Alonso, Diego A. ;
Khoshnood, Abbas .
MOLECULAR CATALYSIS, 2020, 482
[2]   2-Amino-3,5-dicarbonitrile-6-sulfanylpyridines: synthesis and multiple biological activity - a review [J].
Akhmadiev, Nail S. ;
Akhmetova, Vnira R. ;
Ibragimov, Askhat G. .
RSC ADVANCES, 2021, 11 (19) :11549-11567
[3]   Anomeric effect, hyperconjugation and electrostatics: lessons from complexity in a classic stereoelectronic phenomenon [J].
Alabugin, Igor, V ;
Kuhn, Leah ;
Krivoshchapov, Nikolai, V ;
Mehaffy, Patricia ;
Medvedev, Michael G. .
CHEMICAL SOCIETY REVIEWS, 2021, 50 (18) :10212-10252
[4]   Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone [J].
Alabugin, Igor, V ;
Kuhn, Leah ;
Medvedev, Michael G. ;
Krivoshchapov, Nikolai, V ;
Vil', Vera A. ;
Yaremenko, Ivan A. ;
Mehaffy, Patricia ;
Yarie, Meysam ;
Terent'ev, Alexander O. ;
Zolfigol, Mohammad Ali .
CHEMICAL SOCIETY REVIEWS, 2021, 50 (18) :10253-10345
[5]   Metal-Free Multicomponent Syntheses of Pyridines [J].
Allais, Christophe ;
Grassot, Jean-Marie ;
Rodriguez, Jean ;
Constantieux, Thierry .
CHEMICAL REVIEWS, 2014, 114 (21) :10829-10868
[6]   Applications of biological urea-based catalysts in chemical processes [J].
Atashkar, Bahareh ;
Zolfigol, Mohammad Ali ;
Mallakpour, Shadpour .
MOLECULAR CATALYSIS, 2018, 452 :192-246
[7]   Synthesis of Metal-Organic Frameworks MIL-101(Cr)-NH2 Containing Phosphorous Acid Functional Groups: Application for the Synthesis of N-Amino-2-pyridone and Pyrano [2,3-c]pyrazole Derivatives via a Cooperative Vinylogous Anomeric-Based Oxidation [J].
Babaee, Saeed ;
Zarei, Mahmoud ;
Sepehrmansourie, Hassan ;
Zolfigol, Mohammad Ali ;
Rostamnia, Sadegh .
ACS OMEGA, 2020, 5 (12) :6240-6249
[8]   The bohimann-rahtz pyridine synthesis: From discovery to applications [J].
Bagley, Mark C. ;
Glover, Christian ;
Merritt, Eleanor A. .
SYNLETT, 2007, (16) :2459-2482
[9]   Ammonium chloride catalysed one-pot multicomponent synthesis of 1,8-dioxo-octahydroxanthenes and N-aryl-1,8-dioxodecahydroacridines under solvent free conditions [J].
Banerjee, Bubun ;
Brahmachari, Goutam .
JOURNAL OF CHEMICAL RESEARCH, 2014, (12) :745-750
[10]   Facile and Chemically Sustainable One-Pot Synthesis of a Wide Array of Fused O- and N-Heterocycles Catalyzed by Trisodium Citrate Dihydrate under Ambient Conditions [J].
Brahmachari, Goutam ;
Banerjee, Bubun .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (02) :271-286
123456