170288-29-6Relevant academic research and scientific papers
HCl-mediated transamidation of unactivated formamides using aromatic amines in aqueous media
Dhawan, Sanjeev,Girase, Pankaj Sanjay,Kumar, Vishal,Karpoormath, Rajshekhar
, p. 3729 - 3739 (2021/10/14)
We report transamidation protocol to synthesize a range of secondary and tertiary amides from weakly nucleophilic aromatic and hetero-aryl amines with low reactive formamide derivatives, utilizing hydrochloric acid as catalyst. This current acid mediated strategy is beneficial because it eliminates the need for a metal catalyst, promoter or additives in the reaction, simplifies isolation and purification. Notably, this approach conventionally used to synthesize molecules on gram scales with excellent yields and a high tolerance for functional groups.
Copper promoted aerobic oxidative c(sp3)-c(sp3) bond cleavage of n-(2-(pyridin-2-yl)-ethyl)anilines
Yu, Yang,Zhang, Yong,Sun, Chengyu,Shi, Lei,Wang, Wei,Li, Hao
, p. 2725 - 2732 (2020/03/11)
A strategy of aerobic oxidative C(sp3)-C(sp3) bond cleavage of N-ethylaniline derivatives bearing azaarenes for the synthesis of N-aryl formamides has been developed. This approach was carried out smoothly with the CuI/TEMPO/air system to give N-aryl formamides in yields of 50-90%. With this methodology, a mutagenically active compound was constructed in 90% yield. Moreover, the reaction also provided a one-pot synthetic tool for accessing a promoter of hematopoietic stem cells by difunctionalization in 61% yield.
Direct: N -formylation of nitroarenes with CO2
Shen, Ni,Zhai, Shi-Jing,Cheung, Chi Wai,Ma, Jun-An
supporting information, p. 9620 - 9623 (2020/09/03)
Herein we describe a straightforward N-formylation of nitroarenes with CO2 to access N-aryl formamides exclusively in the presence of iron and hydrosilane as additives. This protocol showcases a good tolerance of a wide range of nitroarenes and nitroheteroarenes.
Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides
?koch, Karel,Císa?ová, Ivana,?těpni?ka, Petr
supporting information, p. 13788 - 13791 (2018/09/14)
The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.
Radical perfluoroalkylation - Easy access to 2-perfluoroalkylindol-3-imines-via electron catalysis
Leifert, Dirk,Artiukhin, Denis G.,Neugebauer, Johannes,Galstyan, Anzhela,Strassert, Cristian Alejandro,Studer, Armido
supporting information, p. 5997 - 6000 (2016/05/24)
Arylisonitriles (2 equivalents) react with alkyl and perfluoroalkyl radicals to form 2-alkylated indole-3-imines via two sequential additions to the isonitrile moiety followed by homolytic aromatic substitution. The three component reaction comprises three C-C bond formations. The endocyclic imine functionality in the products is more reactive in follow up chemistry and hydrolysis of the exocyclic imine leads to 3-oxindoles that show fluorescence properties.
Chemoselective Schwartz Reagent Mediated Reduction of Isocyanates to Formamides
Pace, Vittorio,De La Vega-Hernández, Karen,Urban, Ernst,Langer, Thierry
supporting information, p. 2750 - 2753 (2016/06/15)
Addition of the in situ generated Schwartz reagent to widely available isocyanates constitutes a chemoselective, high-yielding, and versatile approach to the synthesis of variously functionalized formamides. Steric and electronic factors or the presence of sensitive functionalities (esters, nitro groups, nitriles, alkenes) do not compromise the potential of the method. Full preservation of the stereochemical information contained in the starting materials is observed. The use of formamides in the nucleophilic addition of organometallic reagents (Chida-Sato allylation, Charette-Huang addition to imidoyl triflate activated amides, Matteson homologation of boronic esters) is briefly investigated.
N-heterocyclic carbene copper(i) catalysed N-methylation of amines using CO2
Santoro, Orlando,Lazreg, Fama,Minenkov, Yury,Cavallo, Luigi,Cazin, Catherine S. J.
, p. 18138 - 18144 (2015/10/28)
The N-methylation of amines using CO2 and PhSiH3 as source of CH3 was efficiently performed using a N-heterocyclic carbene copper(i) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.
A Catalyst-Free Process for the Direct Oxidative Synthesis of Form-anilides from Arylamines and Aldehydes under Air Atmosphere
Qin, Yuancheng,Cheng, Yuanyuan,Luo, Xubiao,Li, Mingjun,Xie, Yu,Gao, Yunhua
supporting information, p. 1900 - 1904 (2015/08/06)
An efficient and catalyst-free process for the direct oxidative synthesis of formanilides from primary aromatic amines and aliphatic aldehydes has been developed under mild aerobic oxidation conditions. The isotope-labeling experiments indicated that the oxygen atom of the formanilide originated from dioxygen.
Highly efficient rhodium-catalyzed transfer hydrogenation of nitroarenes into amines and formanilides
Wei, Yawen,Wu, Jianjun,Xue, Dong,Wang, Chao,Liu, Zhaotie,Zhang, Zhuozhuo,Chen, Guangfu,Xiao, Jianliang
supporting information, p. 1295 - 1298 (2014/06/10)
An efficient and selective rhodium-catalyzed transfer hydrogenation of nitroarenes with formic acid as the hydrogen source to give amines or formanilides has been developed. The addition of iodide ion accelerates the reaction, which can take place at room temperature. Georg Thieme Verlag Stuttgart New York.
PYRIMIDINE DERIVATIVES
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Page/Page column 86, (2011/04/14)
The invention concerns benzamide compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, ring A, n, R3, and R4 are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an antiproliferative agent in the prevention or treatment of tumours or other proliferative conditions which are sensitive to the inhibition of EphB4, and/or EphA2 and/or Src kinases.
