16596-02-4Relevant academic research and scientific papers
ORGANOMETALLIC COMPOUND, LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND ELECTRONIC APPARATUS INCLUDING THE LIGHT-EMITTING DEVICE
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Paragraph 0434-0436; 0445; 0447; 0449-0450, (2022/01/04)
An organometallic compound represented by Formula 1 is provided: [in-line-formulae]M(L1)n1(L2)n2??[Formula 1][/in-line-formulae] [in-line-formulae]*-(T4)a4-(R4)b4??[Formula 2A][/in-line-formulae] L1 in Formula 1 is a ligand represented by Formula 2, Z4 in Formula 2 is represented by Formula 2A, and a complete description of Formulae 1, 2, and 2A is described in the specification. A light-emitting device including the organometallic compound and an electronic apparatus including the light-emitting device are also provided.
Nanoporous TiO2 containing an ionic liquid bridge as an efficient and reusable catalyst for the synthesis of: N, N ′-diarylformamidines, benzoxazoles, benzothiazoles and benzimidazoles
Mazloumi,Shirini,Goli-Jolodar,Seddighi
, p. 5742 - 5752 (2018/04/23)
In this work, a green and efficient procedure is reported for the preparation of N,N'-diarylformamidines, benzoxazoles, benzothiazoles, and benzimidazoles using nanoporous TiO2 containing an ionic liquid bridge. This reagent is prepared via the modification of nanoporous TiO2 with bis-3-(trimethoxysilylpropyl)-ammonium hydrogen sulfate (TiO2-[bip]-NH2+ HSO4-). The procedure gave the products in excellent yields in very short reaction times under solvent-free conditions. The reusability of the catalyst is the other important feature of the reported method.
Catalyst-Free Synthesis of Aryl Diamines via a Three-Step Reaction Process
Bulut, Safak,Queen, Wendy L.
, p. 3806 - 3818 (2018/04/14)
The formation of C-N bonds with aryl amines is one of the most widely studied reactions in organic chemistry. Despite this, it is still highly challenging, often requiring expensive, precious metal-based catalysts. Here we report an easy catalyst-free methodology for constructing C-N bonds. The method, which proceeds via the in situ formation of closed ring amidinium ions, allows the preparation of a series of symmetrical and/or unsymmetrical aryl diamines in notably high yields (82-98%) and purity and with a variety of different substituents. The methodology is shown successful for the preparation of aryl diamines having para- and/or meta-substituted carboxyl, nitro, bromo, methoxy, or methyl groups. This green synthetic pathway, which is catalyst free, requires only three steps, and proceeds without the need for purification. Further, it is a new sustainable, economically viable method to achieve an otherwise challenging bond formation.
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.
Pushing back the limits of hydrosilylation: Unprecedented catalytic reduction of organic ureas to formamidines
Pouessel, Jacky,Jacquet, Olivier,Cantat, Thibault
, p. 3552 - 3556 (2014/01/06)
Pushing back the limits: A novel catalytic transformation has been designed to prepare formamidine derivatives by reduction of substituted ureas with hydrosilanes. Simple iron catalysts based on commercially available iron salts and phosphine ligands prov
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
Orthoamides. LIV. Contributions to the chemistry of azavinylogous orthoformic acid amide derivatives
Kantlehner, Willi,Hauber, Michael,Haug, Erwin,Schallenmueller, Claus,Regele, Claudia
, p. 682 - 699 (2007/10/03)
The azavinylogous aminalester 3 reacts with primary amines to give amidines 5 and 6. In the reaction of 3 with aniline the azavinylogous amidine 7 is produced additionally to the amidine 5c. Ethylendiamine is formylated at both aminogroups, the bis-amidine 8 thus formed is transformed to the salts 9a,b. Benzoxazole and benzimidazole can be prepared from 3 and o-aminophenol and o-phenylenediamine, resp. Carboxylic acid amides, urea, thiourea, aromatic acid hydrazides 17 and the sulfonylhydrazide 19 are formylated by 3 at nitrogen to give N-acylated formamidines 14, 16, 18, 20. From 3 and aliphatic acid hydrazides 17 and alkylhydrazines, resp., can be obtained 1,2,4-triazole 21 and 1-alkyl-1,2,4-triazoles 22a,b, resp. N.N-Dimethylcyanacetamide (32) reacts with 3 and the orthoamide 4a, resp., to give a mixture of the formylated compound 34 and the amidine 33. The reaction conditions are of low influence on the ratio in which 33 and 34 are formed. The orthoamide 4b and 32 react to afford a mixture of the amidine 35 and the enamine 36. Hydrogen-sulfide acts on 3 giving N,N-dimethylthioformamide (37). From 3 and 1-alkynes 41 can be prepared the amidines 42. Hydrolysis of 42b affords phenylpropiolaldehyde (43). The alkylation of the aminalester 3 gives rise to the formation of vinylogous amidinium salts 1c and 1d, resp., additionally is formed the amide acetal 2a. The salt 1d can also be prepared from 3 and borontrifluoride-ether. Iodide reacts with N,N-dimethylformamide acetals 12a,b in an unclear, complicated manner giving orthoesters 53, N,N-dimethylformamide, alkyliodides, alcohols, ammonium iodides 46 and carbondioxide. The action of halogens on 3 affords the salts 1a,b,c,e,f depending on the chosen stoichiometric ratio. Aromatic aldehydes are suited for trapping azavinylogous carbenes formed on thermolysis of 3; 1,3-oxazoles 69 are the reaction products. From 3 and propionaldehyde the amidine 65 can be obtained with low yield. Carbondisulfide transforms 3 to the azavinylogous salt 66. The preparation of the azavinylogous orthoamide 4a is described. The thermolysis of 3 and 4a, resp., gives rise to the formation of the triaminopyrimidine 67. Treatment of 1a with lithium diisopropylamide affords the triaminopyrazine 68, which can also be obtained by thermolysis of 3 in the presence of sodium hydride. Azavinylogous carbenes are thought to be the intermediates. Wiley-VCH Verlag GmbH, 2000.
Raney Nickel Desulphuration of 1-Substituted- and 1,3-Disubstituted-thioureas
Ali, M. Umar,Meshram, H. M.,Paranjpe, M. G.
, p. 666 - 669 (2007/10/02)
Certain 1-aryl-1,3-diaryl- and 1-aryl-3-tetra-O-acetyl-β-D-glucopyranosyl thioureas have been successfully desulphurated into the related mono- and 1,3-di-substituted formamidines with the help of Raney nickel catalyst.A few of them have been converted into the corresponding formamides also.Structure of the products have been established through usual chemical transformations, ir, nmr and mass spectral analysis.
Raney Nickel Desulphuration of Some 1-Arylthioureas
Ali, M. Umar,Paranjpe, M. G.
, p. 573 - 574 (2007/10/02)
1-Arylthioureas (I) undergo desulphuration in boiling ethanol in the presence of Raney nickel (W-2) to give the corresponding arylformamides (IV) and arylamines (III).A probable mechanism for the formation of these products has been suggested.
