Zn(II) anchored onto the magnetic natural hydroxyapatite (ZnII/HAP/Fe3O4): as a novel, green and recyclable catalyst for A3-coupling reaction towards propargylamine synthesis under solvent-free conditions

被引:61
作者
Zarei, Zeinab [1 ]
Akhlaghinia, Batool [1 ]
机构
[1] Ferdowsi Univ Mashhad, Dept Chem, Fac Sci, Mashhad 9177948974, Iran
关键词
ONE-POT SYNTHESIS; C-H ACTIVATION; 3-COMPONENT COUPLING REACTION; EFFICIENT HETEROGENEOUS CATALYST; ALDEHYDE-ALKYNE-AMINE; TERMINAL ALKYNES; REUSABLE CATALYST; DIRECT-ADDITION; ENANTIOSELECTIVE SYNTHESIS; SECONDARY-AMINES;
D O I
10.1039/c6ra20501a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this paper, Zn(II) anchored onto the magnetic natural hydroxyapatite (ZnII/HAP/Fe3O4), as a new, versatile and magnetically recoverable catalyst, was prepared and characterized using different techniques such as FT-IR, XRD, TGA, TEM, EDX, VSM and ICP. The composition of this catalyst was determined and it was clearly found that the size of the particles was about 8-30 nm and they were rod-like in shape. Also, VSM analysis showed that the synthesized nanocatalyst had superparamagnetic behavior. The new nanocatalyst has been found to effectively catalyze the synthesis of structurally different propargylamine derivatives via a one-pot three-component A(3)-coupling reaction of terminal alkynes, aldehydes and secondary amines in high yields at 100 degrees C under solvent-free conditions. This green protocol provides significant advantages, such as excellent yield of products, broad substrate scope, mild reaction conditions, minimization of chemical waste, simple work-up procedure, easy preparation of catalyst and being environmentally benign. Importantly, the prepared nanocatalyst can be recovered by applying an external magnetic field and reused for seven cycles without significant loss of activity.
引用
收藏
页码:106473 / 106484
页数:12
相关论文
共 158 条
[91]   Nickel-Catalyzed Solvent-Free Three-Component Coupling of Aldehyde, Alkyne and Amine [J].
Namitharan, Kayambu ;
Pitchumani, Kasi .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (03) :411-415
[92]  
Nikje M., 2015, International Journal of Nanoscience and Nanotechnology, V11, P39
[93]   Copper-catalyzed coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation [J].
Niu, Mingyu ;
Yin, Zhengming ;
Fu, Hua ;
Jiang, Yuyang ;
Zhao, Yufen .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (10) :3961-3963
[94]   Direct Enantioselective Three-Component Synthesis of Optically Active Propargylamines in Water [J].
Ohara, Mutsuyo ;
Hara, Yoshichika ;
Ohnuki, Tohru ;
Nakamura, Shuichi .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (29) :8848-8851
[95]   An efficient synthesis of propargylamines via C-H activation catalyzed by copper(I) in ionic liquids [J].
Park, SB ;
Alper, H .
CHEMICAL COMMUNICATIONS, 2005, (10) :1315-1317
[96]   Copper zeolites as green catalysts for multicomponent reactions of aldehydes, terminal alkynes and amines: An efficient and green synthesis of propargylamines [J].
Patil, Meghshyam K. ;
Keller, Murielle ;
Reddy, Benjaram M. ;
Pale, Patrick ;
Sommer, Jean .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (26) :4440-4445
[97]   Cationic Gold- and Silver-Catalyzed Cycloisomerizations of Propargylic Ureas: A Selective Entry to Oxazolidin-2-imines and Imidazolidin-2-ones [J].
Pereshivko, Olga P. ;
Peshkov, Vsevolod A. ;
Jacobs, Jeroen ;
Van Meervelt, Luc ;
Van der Eycken, Erik V. .
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (04) :781-789
[98]   Nano indium oxide catalyzed efficient synthesis of propargylamines via C-H and C-Cl bond activations [J].
Rahman, Matiur ;
Bagdi, Avik Kr ;
Majee, Adinath ;
Hajra, Alakananda .
TETRAHEDRON LETTERS, 2011, 52 (34) :4437-4439
[99]   Zn(OAc)2•2H2O:: a versatile catalyst for the one-pot synthesis of propargylamines [J].
Ramu, Enugala ;
Varala, Ravi ;
Sreelatha, Nuvula ;
Adapa, Srinivas R. .
TETRAHEDRON LETTERS, 2007, 48 (40) :7184-7190
[100]   Hydroxyapatite nanoparticles (HAP NPs): a green and efficient heterogeneous catalyst for three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media [J].
Razavi, Nasrin ;
Akhlaghinia, Batool .
NEW JOURNAL OF CHEMISTRY, 2016, 40 (01) :447-457