165402-17-5Relevant articles and documents
A ZnI2-catalyzed regioselective cascade 1,4-conjugate addition/5-: Exo-dig annulation pathway for one-pot access to heterobiaryl frameworks
He, Xinwei,Choy, Pui Ying,Leung, Man Pan,Yuen, On Ying,Liu, Tianyi,Shang, Yongjia,Kwong, Fuk Yee
, p. 15069 - 15072 (2019)
Facile access to π-extended heterobiaryl compounds via a non-cross-coupling strategy has been achieved. In the presence of an inexpensive ZnI2 catalyst and versatile propargylamine and β-naphthol (or β-naphthylamine and β-naphthyl mercaptan) starting materials, a variety of sterically hindered heterobiaryl frameworks can be easily obtained. The present catalytic system offers excellent selectivity, good-to-excellent product yields, and good functional group tolerance including, for instance, -CN, -COOH, -C(O)R, -Br and -Cl groups. This cyclization process is proposed to proceed via in situ generated alkynyl o-quinone methides (o-AQMs), following a cascade intermolecular 1,4-conjugate addition/5-exo-dig annulation/1,3-H shift pathway.
Effect of the ortho-hydroxy group of salicylaldehyde in the A3 coupling reaction: A metal-catalyst-free synthesis of propargylamine
Ghosh, Sujit,Biswas, Kinkar,Bhattacharya, Suchandra,Ghosh, Pranab,Basu, Basudeb
, p. 552 - 557 (2017)
The synthesis of propargylamines via A3 coupling mostly under metal-catalyzed procedures is well known. This work invented an unprecedented effect of salicylaldehyde, one of the A3 coupling partners, which could lead to the formation
Metal- And Solvent-Free Multicomponent Decarboxylative A3-Coupling for the Synthesis of Propargylamines: Experimental, Computational, and Biological Investigations
Gurjar, Kamlesh K.,Kaur, Pavneet,Kumar, Bhupinder,Kumar, Rakesh,Kumar, Rohtash,Kumar, Vinod
, (2020)
Decarboxylative A3-coupling of ortho-hydroxybenzaldehydes, secondary amines, and alkynoic acids is performed under catalyst and solvent-free conditions. The developed methodology provided a waste-free method for the synthesis of hydroxylated pr
Investigation into the Catalytic Performance of Cu(II) Supported Graphene Quantum Dots Modified NiFe2O4 as a Proficient Nano-Catalyst in the Synthesis of Propargylasmines
Monajjemifar, Soudabeh,Moeinpour, Farid,Mohseni-Shahri, Fatemeh S.
, p. 1444 - 1455 (2020/10/02)
Abstract: NiFe2O4 nanoparticles are modified by graphene quantum dots (GQDs) and utilized to stabilize the Cu(II) nanoparticles as a novel magnetically retrievable catalytic system (Cu(II)/GQDs/NiFe2O4) for gree
Cascade Lactonization/Benzannulation of Propargylamines with Dimethyl 3-Oxoglutarate for Modular Assembly of Hydroxylated/Arene-Functionalized Benzo[ c]chromen-6-ones
Duan, Jiahui,He, Xinwei,Choy, Pui Ying,Wang, Qi,Xie, Mengqing,Li, Ruxue,Xu, KeKe,Shang, Yongjia,Kwong, Fuk Yee
supporting information, p. 6455 - 6460 (2021/08/23)
A DBU-mediated cascade strategy of propargylamines with dimethyl 3-oxoglutarate for constructing a functionalized benzo[c]chromen-6-one core has been achieved. This cascade process presumably involves a sequence of 1,4-conjugate addition, followed by lact
Solvent-free synthesis of propargylamines via A3 coupling reaction and organic pollutant degradation in aqueous condition using Cu/C catalyst
Rathod, Pramod V.,Puguan, John Marc C.,Kim, Hern
, (2020/09/04)
The present report focuses on the efficient and operationally simple synthesis of biomass-derived carbon as support to immobilize copper particles as a catalyst for the one-pot synthesis of propargylamines from furfural via the A3 coupling reaction. This new catalyst showed remarkable catalytic performance leading to a 97% yield within 5 h at 80 °C using 5 mg (0.0022 mmol Cu) of Cu/C catalyst under solvent-free condition. Moreover, nitro-substituted compounds such as 4-nitrophenol (4-NP) are highly toxic and not easily degradable. Hence, a quick and effective method is required to neutralize these toxic compounds. The synthesized active support Cu/C catalyst having various electron-donating groups containing small amounts of Cu plays an essential role in the catalytic reduction of 4-NP (0.1 g). Using only 3 mg (0.0013 mmol Cu) of Cu/C catalyst and NaBH4 (10 mmol), a 99% yield (100% selectivity) in the aqueous condition at 25 °C was achieved. The catalytic reduction follows the pseudo-first-order kinetics with reaction rate constant of 0.028 s?1. Moreover, results demonstrate that the Cu/C catalyst has superior catalytic activity due to the presence of electron-donating molecules such as O, S, and N atoms, which enable synergistic effect in enhancing the overall catalytic performance. Notably, the recoverability and recyclability of the synthesized catalyst were evaluated for up to four cycles, which confirmed its stability in these cycles.
One-pot three-component synthesis of propargylamines using an efficient and reusable copper bio-functionalized magnetic graphene oxide nanocomposite
Rafiee, Fatemeh,Khavari, Parvaneh
, (2020/01/02)
In this work, magnetic graphene oxide was produced through chemical oxidation of the graphite powder, exfoliation under ultrasonic waves and then magnetization in the presence of ion salts. Magnetic graphene oxide was functionalized with cysteine and used
Synthesis and characterization of magnetic glycocyamine-modified chitosan as a biosupport for the copper immobilization and its catalytic activity investigation
Rafiee,Karder, F. Rezaie
, (2019/11/29)
Trichloro-1,3,5-triazine agent was used for chitosan functionalization and as a bridge between the functionalized chitosan and glycocyamine to form a bio ligand for the copper coordination. The magnetization of modified chitosan was done using of Fe3
Reduced graphene oxide-immobilized iron nanoparticles Fe(0)@rGO as heterogeneous catalyst for one-pot synthesis of series of propargylamines
Kujur, Shelly,Pathak, Devendra Deo
, p. 369 - 384 (2019/08/28)
Abstract: Iron nanoparticles immobilized on reduced graphene oxide (rGO), nanocomposite Fe(0)@rGO 1, were prepared in situ by reduction of GO and FeCl3·6H2O using sodium borohydride under nitrogen atmosphere. The nanocomposite 1 was
Synthesis of polyhydroquinolines and propargylamines through one-pot multicomponent reactions using an acidic ionic liquid immobilized onto magnetic Fe3O4as an efficient heterogeneous catalyst under solvent-free sonication
Nguyen, Hai Truong,Tran, Phuong Hoang,Truong, Vy Anh
, p. 25358 - 25363 (2020/07/30)
A nano-sized Fe3O4-supported Lewis acid ionic liquid catalyst for the synthesis of polyhydroquinolines and propargylamines under ultrasound irradiation has been developed. LAIL&at;MNP was synthesized from imidazolium chlorozincate(ii) ionic liquid grafted onto the surface of Fe3O4 nanoparticles and evaluated by FT-IR, TGA, SEM, Raman, TEM, ICP-OES, and EDS. The multicomponent synthesis of polyhydroquinolines and propargylamines proceeded smoothly to afford the desired products in high yields. LAIL&at;MNP can be separated easily from the reaction mixture and reused for several runs without a significant degradation in catalytic activity.
