scholarly journals Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation

2016 ◽  
Vol 12 ◽  
pp. 1493-1502 ◽  
Author(s):  
Erika Bálint ◽  
Ádám Tajti ◽  
Anna Dzielak ◽  
Gerhard Hägele ◽  
György Keglevich

A practical method was elaborated for the synthesis of (aminomethylene)bisphosphine oxides comprising the catalyst- and solvent-free microwave-assisted three-component condensation of primary amines, triethyl orthoformate and two equivalents of diphenylphosphine oxide. The method is also suitable for the preparation of (aminomethylene)bisphosphonates using (MeO)2P(O)H/(MeO)3CH or (EtO)2P(O)H/(EtO)3CH reactant pairs and even secondary amines. Several intermediates referring to the reaction mechanism together with a few by-products could also be identified.

2017 ◽  
Vol 13 ◽  
pp. 76-86 ◽  
Author(s):  
Erika Bálint ◽  
Ádám Tajti ◽  
Anna Ádám ◽  
István Csontos ◽  
Konstantin Karaghiosoff ◽  
...  

A family of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides was synthesized by the microwave-assisted solvent-free addition of dialkyl phosphites and diphenylphosphine oxide, respectively, to imines formed from benzaldehyde derivatives and primary amines. After optimization, the reactivity was mapped, and the fine mechanism was evaluated by DFT calculations. Two α-aminophosphonates were subjected to an X-ray study revealing a racemic dimer formation made through a N–H···O=P intermolecular hydrogen bridges pair.


2005 ◽  
Vol 2005 (1) ◽  
pp. 27-28 ◽  
Author(s):  
Jaime Charris ◽  
Arthur Barazarte ◽  
José Domínguez ◽  
Neira Gamboa

A rapid method for the preparation of N-aryl-2-methylthio-4-oxo-1,4-dihydro quinoline-3-carbonitriles (2a–e) and N-aryl-3-methylthio-4H-1,4-benzothiazine-2-carbonitrile 1,1-dioxides (2f–o) is reported. The cyclization is accelerated by microwave irradiation under solvent free conditions in the presence of K2CO3.


2011 ◽  
Vol 22 (12) ◽  
pp. 2396-2402 ◽  
Author(s):  
Jorge E. Trilleras ◽  
Kelly J. Velasquez ◽  
Dency J. Pacheco ◽  
Jairo Quiroga ◽  
Alejandro Ortíz

2018 ◽  
Vol 73 (1) ◽  
pp. 43-74 ◽  
Author(s):  
Cindy Döring ◽  
Peter G. Jones

AbstractThe reaction of (tht)AuX (X=Cl or Br; tht=tetrahydrothiophene) with various primary amines L leads to products of the form [L2Au]+X−. Packing diagrams of the corresponding structures are dominated by N–H···X hydrogen bonds and (in some cases) aurophilic contacts. The cyclohexylamine derivative was already known as its dichloromethane ⅔-solvate; we have isolated the solvent-free compound and its pentane ¼-solvate, which all show different packing patterns. With acyclic secondary amines, the products are more varied; LAuX and [L2Au]+[AuX2]− were also found. These gold(I) products were generally formed in satisfactory quantities. The attempted oxidation to Au(III) derivatives with PhICl2 or Br2 proved impossible for the primary amine derivatives [although isopropylamine-trichloridogold(III) was obtained unexpectedly from the corresponding cyanide] and unsatisfactory for the secondary amine derivatives. Products LAuX3 and [L2AuX2]+[AuX4]− were identified but were formed in disappointing yields. In isolated cases protonated products (LH)+[AuCl4]−, (LH+)3[AuCl4]−(Cl−)2 or [(Et2N)2CH]+[AuBr4]− were formed, presumably by involvement of the dichloromethane solvent and/or adventitious water. Here also the yields were poor, and some products arose as mixtures. Direct reaction of amines with AuCl3 or (tht)AuX3 was also unsuccessful. All products were characterized by X-ray structure analysis.


ChemInform ◽  
2008 ◽  
Vol 39 (34) ◽  
Author(s):  
Xiao-Jian Wang ◽  
Qian Yang ◽  
Fei Liu ◽  
Qi-Dong You

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