18522-98-0Relevant academic research and scientific papers
Sustainable carbonecarbon bond formation catalyzed by new oxamate-containing palladium(II) complexes in ionic liquids
Fortea-Pérez, Francisco Ramón,Schlegel, Isabel,Julve, Miguel,Armentano, Donatella,De Munno, Giovanni,Stiriba, Salah-Eddine
, p. 102 - 108 (2013)
New and versatile bis(oxamato)palladate(II) complexes of formula (n-Bu 4N)2[Pd(2-Mepma)2]·4H2O (1a) and (n-Bu4N)2[Pd(4-Mepma)2]·2H 2O·MeCN (1b) (n-Bu4N+ = tetra-n-buthylammonium, 2-Mepma = N- 2-methylphenyloxamate and 4-Mepma = N-4-methylphenyloxamate) have been synthesized and characterized by spectroscopic methods and single crystal X-ray diffraction. Each palladium(II) ion in 1a and 1b is four-coordinate with two oxygen and two nitrogen atoms from two fully deprotonated oxamate ligands building a centrosymmetric square planar surrounding. Their catalytic role has been investigated for both Heck and Suzuki coupling reactions using a series of aryl iodide/bromide derivatives in tetra-n-butylammonium bromide (n-Bu 4NBr) as ionic liquid, i.e. molten salt. These precatalysts appear as highly efficient, easily recovered and reused at least eight times without any drastic loss of their exceptional reactivity or leaching from the ionic liquid medium.
Carbamoyl Radicals via Photoredox Decarboxylation of Oxamic Acids in Aqueous Media: Access to 3,4-Dihydroquinolin-2(1 H)-ones
Bai, Qi-Fan,Jin, Chengan,He, Jing-Yao,Feng, Gaofeng
supporting information, p. 2172 - 2175 (2018/04/30)
The first visible-light-mediated photoredox oxidative approach for generating carbamoyl radicals from oxamic acids is disclosed. Reaction of the generated carbamoyl radicals with electron-deficient alkenes opens efficient access to 3,4-dihydroquinolin-2(1H)-ones under mild conditions through a sequence of intermolecular radical addition, cyclization, and aromatization. The process is compatible with a variety of oxamic acids and electron-deficient alkenes, and a wide variety of 3,4-dihydroquinolin-2(1H)-ones were prepared.
A copper/O2-mediated direct sp3 C-H/N-H cross-dehydrogen coupling reaction of acylated amines and: N -aryl glycine esters
Sun, Bin,Wang, Yao,Li, Deyu,Jin, Can,Su, Weike
supporting information, p. 2902 - 2909 (2018/05/03)
A copper salt-catalyzed cross-dehydrogenative coupling reaction between N-aryl glycine esters and acylated amines has been developed. The reaction proceeded effectively under an oxygen atmosphere without the use of peroxide agents. This simple protocol al
2,2,2-Trifluoroethyl Chlorooxoacetate-Universal Reagent for One-Pot Parallel Synthesis of N1-Aryl-N2-alkyl-Substituted Oxamides
Bogolubsky, Andrey V.,Moroz, Yurii S.,Mykhailiuk, Pavel K.,Pipko, Sergey E.,Zhemera, Anton V.,Konovets, Anzhelika I.,Stepaniuk, Olena O.,Myronchuk, Inna S.,Dmytriv, Yurii V.,Doroschuk, Roman A.,Zaporozhets, Olga A.,Tolmachev, Andrey
, p. 615 - 622 (2015/10/28)
A one-pot parallel synthesis of N1-aryl-N2-alkyl-substituted oxamides with 2,2,2-trifluoroethyl chlorooxoacetate was developed. The synthesis of a library of 45 oxamides revealed higher efficiency of this reagent over the known ethyl chlorooxoacetate. The reagent was successfully used to prepare the known oxamide-containing HIV entry inhibitors.
Highly efficient dehydrogenative cross-coupling of aldehydes with amines and alcohols
Deshidi, Ramesh,Rizvi, Masood Ahmad,Shah, Bhahwal Ali
, p. 90521 - 90524 (2015/11/11)
A common protocol for the synthesis of amides, esters and α-ketoesters via cross dehydrogenative coupling of aldehydes and amines/alcohols has been developed. The method is applicable to a wide variety of alcohols and amines as well as aliphatic and aromatic aldehydes. Also, the use of acetaldehyde for acetylation and ethyl glyoxalate to access 2-oxo-amino esters is presented for the first time.
Improved microwave synthesis of unsymmetrical N,N'-diaryl-1,2-aminoethane and imidazolidinium salts as precursors of N-heterocyclic carbenes
Ibrahim, Yehia A.,Al-Awadi, Nouria A.,Al-Azemi, Talal F.,John, Elizabeth
, p. 38869 - 38876 (2014/11/08)
Lithium aluminium hydride reduction of bis-unsymmetric-diaryloxamides 3 is difficult to accomplish especially for the sterically hindered mesityl derivative. Using microwaves LAH reduction of 3a,d was successful in a short time, however, with cleavage of the ether linkage to give compounds 11a,d. Extension of this method enabled the reduction of bis-oxamide derivatives 13 to the corresponding tetraamine derivative 14 which was then converted to the bis-imidazolidinium salt 15. Application of this method led to rapid reduction of unsymmetric N,N'-diaryloxamides 16 to the corresponding N,N'- diarylethylenediamines 17 which were converted to their corresponding imidazolidinium salts 18. the Partner Organisations 2014.
Auto-oxidative coupling of glycine derivatives
Huo, Congde,Yuan, Yong,Wu, Mingxia,Jia, Xiaodong,Wang, Xicun,Chen, Fengjuan,Tang, Jing
supporting information, p. 13544 - 13547 (2015/01/09)
The unprecedented title reaction between glycine derivatives and indoles, as well as the auto-oxidative Povarov/ aromatization tandem reaction of glycine derivatives with olefins are described. The reactions were performed in the absence of redox-active c
A transformation of N-alkylated anilines to N-aryloxamates
Zhu, Xiao-He,Zhang, Xin,Xin, Hong-Xing,Yan, Hong
, p. 1542 - 1547 (2013/09/02)
Transformation of N-alkylated anilines to N-aryloxamates was studied using ethyl 2-diazoacetoacetate as an alkylating agent and dirhodium tetraacetate (Rh2(OAc)4) as the catalyst. The general applicability of the reaction as a synthetic method for N-aryloxamates was studied with a number of substituted N-alkylated anilines. The results revealed that the oxamate was formed by a radical reaction with molecular O2 and Rh 2(OAc)4 as initiator. Copyright
Iron-catalyzed oxidative tandem reactions with TEMPO oxoammonium salts: Synthesis of dihydroquinazolines and quinolines
Rohlmann, Renate,Stopka, Tobias,Richter, Heinrich,Garcia Mancheno, Olga
, p. 6050 - 6064 (2013/07/26)
A straightforward iron-catalyzed divergent oxidative tandem synthesis of dihydroquinazolines and quinolines from N-alkylanilines using a TEMPO oxoammonium salt as a mild and nontoxic oxidant has been developed. Fe(OTf) 2 was the Lewis acid cata
New Highlights in the Synthesis of 4-Aryl-1,4-dihydropyrazines
He, Jing-Yu,Song, Xiu-Qing,Yan, Hong,Zhong, Ru-Gang
, p. 1357 - 1361 (2013/02/23)
The 4-aryl-1,4-dihydropyrazines were prepared via the cyclization of N,N-bisalkylated anilines with ammonium acetate. These reactions were aided by improvements in the synthesis of N,N-bisalkylated anilines which were alkylated with anilines using ethyl 2-diazo acetoacetate in a reaction catalyzed by rhodium acetate in the absence of oxygen. A possible mechanistic route is postulated on the basis of the isolation of the N-alkylation intermediates, which were determined to be N-aryloxamates by 1H NMR data and X-ray diffraction.
