16596-01-3Relevant academic research and scientific papers
Ionic liquid-functionalized mesoporous silica nanoparticles ([pmim]FeCl4/MSNs): Efficient nanocatalyst for solvent-free synthesis of N,N′-diaryl-substituted formamidines
Nasresfahani, Zahra,Kassaee, Mohammad Zaman,Eidi, Esmaiel
, (2017/10/05)
We report the synthesis of ionic liquid-functionalized mesoporous silica nanoparticles ([pmim]FeCl4/MSNs) via a method of post-grafting on parent MSNs. This hybrid material was characterized using scanning and transmission electron microscopies, energy-dispersive X-ray spectroscopy, nitrogen adsorption–desorption analysis, Fourier transform infrared spectroscopy, powder X-ray diffraction and thermal analyses. The material was utilized as an efficient heterogeneous catalyst for the synthesis of N,N′-diaryl-substituted formamidines through the reaction of triethyl orthoformate with arylamines under solvent-free conditions. The catalyst was recovered easily and reused several times without significant loss of its catalytic activity.
Structures, Electronics, and Reactivity of Strained Phosphazane Cages: A Combined Experimental and Computational Study
Roth, Torsten,Vasilenko, Vladislav,Wadepohl, Hubert,Wright, Dominic S.,Gade, Lutz H.
supporting information, p. 7636 - 7644 (2015/08/11)
A series of formamidine-bridged P2N2 cages have been prepared. Upon deprotonation, these compounds serve as valuable precursors to hybrid N-heterocyclic carbene ligands, whereas direct metalation gives rearranged dimetallic complexes as a result of cleavage of the formamidine bridge. The latter metal complexes contain an intact cyclophosphazane moiety that coordinates two distinct metal centers in a monodentate and a chelating fashion. A computational study has been carried out to elucidate the bonding within the P2N2 framework as well as the reactivity patterns. Natural bond orbital analysis indicates that the cage motif is poorly described by localized Lewis structures and that negative hyperconjugation effects govern the stability of the bicyclic framework. The donor capacity of the cyclophosphazane unit was assessed by inspection of the frontier molecular orbitals, highlighting the fact that π-back-donation from the metal fragments is crucial for effective metal-ligand binding.
Ultrasound promoted expeditious, catalyst-free and solvent-free approach for the synthesis of N,N′-diarylsubstituted formamidines at room temperature
Dar, Bashir Ahmad,Ahmad, Syed Naseer,Wagay, Mohammad Arif,Hussain, Altaf,Ahmad, Nisar,Bhat, Khursheed Ahmad,Khuroo, Mohammad Akbar,Sharma, Meena,Singh, Baldev
, p. 4880 - 4884 (2013/09/02)
An effortless and efficient protocol was developed for the synthesis of N,N′-diarylsubstituted formamidines under environment-friendly conditions. Ultrasonic energy was employed to obtain the desired products in excellent yields with high purity under solvent-free and catalyst-free conditions. Products were purified by the crystallization technique to avoid excess utilization of organic solvents.
Multicomponent synthesis of 1-aryl 1,2,4-triazoles
Tam, Annie,Armstrong, Ian S.,La Cruz, Thomas E.
supporting information, p. 3586 - 3589 (2013/08/23)
A multicomponent (single reactor) process for the synthesis of 1-aryl 1,2,4-triazoles was explored and developed. This transformation prepared the 1,2,4-triazole directly from anilines, amino pyridines, and pyrimidines. The reaction scope was explored with 21 different substrates, and the position of the nitrogen atoms in the newly formed ring was established by 15N labeling and NMR spectroscopy.
Biomimetic approach for the synthesis of N,N′-diarylsubstituted formamidines catalyzed by β-cyclodextrin in water
Patil, Dipak R.,Dalal, Dipak S.
, p. 1125 - 1128 (2012/11/13)
An environmentally benign and highly efficient biomimetic approach for the synthesis of N,N′-diarylsubstituted formamidines in water catalyzed β-cyclodextrin is described under neutral condition with quantitative yields of products. β-Cyclodextrin has bee
Deep eutectic solvent promoted highly efficient synthesis of N, N'-diarylamidines and formamides
Azizi, Najmadin,Gholibeglo, Elham,Babapour, Mahbobe,Ghafuri, Hossein,Bolourtchian, Seyed Mohammad
, p. 768 - 773 (2012/10/30)
A deep eutectic solvent was used as a dual catalyst and reaction medium for the efficient N-formylation of aromatic amines without hazardous organic solvent and catalyst. Treatment of aromatic amines with trimethyl orthoformate and formic acid in deep eutectic solvent at 70 °C gives the corresponding N-formyl derivatives in good to excellent yields. This simple ammonium deep eutectic solvent, easily synthesized from choline chloride and SnCl2, with 100% atom economy and making it applicable to industry and laboratory. Furthermore, heating the trimethyl orthoformate and aromatic primary amines in the deep eutectic solvent results in formation of the corresponding N,N'-diarylamidines in high yields.
Facile synthesis of hydroxyformamidines by the N-oxidation of their corresponding formamidines
Cibian, Mihaela,Langis-Barsetti, Sophie,Hanan, Garry S.
supporting information; experimental part, p. 405 - 409 (2011/04/22)
The N-oxidation of N,N-disubstituted amidines with MCPBA (m-chloroperoxibenzoic acid) affords a mild, rapid, and efficient route to the corresponding hydroxyamidines This novel synthetic route for the preparation of N,N-disubstituted hydroxyamidines provi
An efficient synthesis of imidazolinium salts using vinyl sulfonium salts
McGarrigle, Eoghan M.,Fritz, Sven P.,Favereau, Ludovic,Yar, Muhammad,Aggarwal, Varinder K.
supporting information; experimental part, p. 3060 - 3063 (2011/07/31)
The synthesis of imidazolinium salts from the reaction of formamidines and (2-bromoethyl)diphenylsulfonium triflate is described. A variety of symmetrical and unsymmetrical imidazolinium triflate salts were synthesized in high yield in short reaction time
Introduction of azetidinimine skeleton on C60
Ueda, Nobuaki,Nikawa, Hidefumi,Takano, Yuta,Ishitsuka, Midori O.,Tsuchiya, Takahiro,Akasaka, Takeshi
experimental part, p. 426 - 431 (2012/01/06)
The azacyclobutane structure is introduced into C60 fullerene using a photochemical reaction with formamidines. Three azetidinofullerenes (2c-2e) were synthesized; their molecular structures were characterized using 1H, 13
A modular synthesis of highly substituted imidazolium salts
Hirano, Keiichi,Urban, Slawomir,Wang, Congyang,Glorius, Frank
supporting information; experimental part, p. 1019 - 1022 (2009/07/18)
A versatile and modular one-pot method for the preparation of differently substituted symmetrical and unsymmetrical imidazolium salts is reported, and 19 examples are given. In the key step, readily available formamidines and α-halo ketones are coupled to give imidazolinium salts 3, followed by imidazolium salt formation by acylation-induced elimination. For many substitution patterns of the imidazolium salt products, this efficient strategy compares favorably with well-known processes in terms of yield, ease of synthesis, and robustness.
