72787-99-6Relevant academic research and scientific papers
Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution
Wang, Jin,Hou, Huiqing,Hu, Yongzhi,Lin, Jin,Wu, Min,Zheng, Zhiqiang,Xu, Xiuzhi
supporting information, (2021/02/09)
A novel visible-light-promoted N-acylation for the synthesis of amides from easily available carboxylic acids with amines in the presence of I2 within 2.5 h in aqueous solution has been developed. Using sunlight as the visible light source greatly reduces the cost of experiments and produces almost no toxic effects. Hence, this study provides an alternative catalytic system for the construction of a wide range of amides with readily available materials. Moreover, the strategy was successfully applied in the preparation of N-(3-(2,6-dimethoxyphenoxy)-7-nitroquinoxalin-2-yl)benzohydrazide, which displayed a signification anti-proliferation effect on A549, MCF-7 and HCT116 cell lines.
Direct C-H aminocarbonylation ofN-heteroarenes with isocyanides under transition metal-free conditions
Zhou, Zhong,Ji, Huihui,Li, Qing,Zhang, Qian,Li, Dong
supporting information, p. 2917 - 2922 (2021/04/14)
A C-C bond forming amide synthesis through direct C-H aminocarbonylation ofN-heteroarenes with isocyanides was developed. The reaction was mediated by an inorganic persulfate salt under transition metal-free conditions. Mechanistic studies suggested a radical pathway for this reaction without the participation of H2O and O2. This method also showed merits of substrate availability, easy operation and atom economy. It provided an efficient route for straightforward synthesis ofN-heteroaryl amides.
Preparation method of isoquinoline-1-formamide compounds
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Paragraph 0043-0046, (2021/07/08)
The invention relates to a preparation method of isoquinoline-1-formamide compounds. The preparation method comprises the following steps: mixing an oxidant, a reactant I, a reactant II and a solvent in a reactor, carrying out amidation reaction, and separating and purifying after the reaction to obtain the isoquinoline-1-formamide compounds, wherein the oxidizant is persulfate; the reactant I is an isoquinoline compound; and the reactant II is optionally selected from tert-butyl isocyanide, phenyl isocyanide and cyclohexyl isocyanide. The method is mild in reaction condition, high in selectivity, relatively high in yield and environment-friendly. Through detection, the synthesized isoquinoline-1-formamide compounds have certain biological activity and can be applied to the fields of drug synthesis, pesticide synthesis, paint and dye synthesis and the like.
Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary Amines
Yang, Qi-Liang,Wang, Xiang-Yang,Lu, Jia-Yan,Zhang, Li-Pu,Fang, Ping,Mei, Tian-Sheng
supporting information, p. 11487 - 11494 (2018/09/13)
Electrochemical oxidation represents an environmentally friendly solution to conventional methods that require caustic stoichiometric chemical oxidants. However, C-H functionalizations merging transition-metal catalysis and electrochemical techniques are, to date, largely confined to the use of precious metals and divided cells. Herein, we report the first examples of copper-catalyzed electrochemical C-H aminations of arenes at room temperature using undivided electrochemical cells, thereby providing a practical solution for the construction of arylamines. The use of n-Bu4NI as a redox mediator is crucial for this transformation. On the basis of mechanistic studies including kinetic profiles, isotope effects, cyclic voltammetric analyses, and radical inhibition experiments, the reaction appears to proceed via a single-electron-transfer (SET) process, and a high valent Cu(III) species is likely involved. These findings provide a new avenue for transition-metal-catalyzed electrochemical C-H functionalization reactions using redox mediators.
Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides
He, Zeng-Yang,Huang, Chao-Fan,Tian, Shi-Kai
supporting information, p. 4850 - 4853 (2017/09/23)
The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.
Copper-catalyzed carboxamide-directed ortho amination of anilines with alkylamines at room temperature
Li, Qiong,Zhang, Shu-Yu,He, Gang,Ai, Zhaoyan,Nack, William A.,Chen, Gong
supporting information, p. 1764 - 1767 (2014/04/17)
In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.
ELECTROCHEMICAL REDUCTION OF PRISTINAMYCIN IA AND RELATED STREPTOGRAMINS IN AQUEOUS ACIDIC MEDIUM
Largeron, M.,Vuilhorgne, M.,Potier, I. Le,Auzeil, N.,Bacque, E.,and al.
, p. 6307 - 6332 (2007/10/02)
The electrochemical reduction of the picolinoyl residue of pristinamycinIA and related streptogramins was performed at a mercury cathode, in aqueous medium.The presence of a peptidic lactone residue at the amide nitrogen atom markedly modified the expected cathodic behaviour of pyridyl carboxamides: in particular, we observed the reduction of the pyridyl ring into tetrahydropyridine derivatives.Thanks to a series of model heterocyclic carboxamides, increasing steric hindrance at the amide nitrogen position was shown to lead to enhanced reduction of the heterocyclic ring.
Some Reactions of N-Alkoxycarbonyl Reissert Compounds with Heterocumulenes: Formation of the Imidazoisoquinoline and Imidazophthalazine Systems and Related Chemistry
Uff, Barrie C.,Budhram, Ronald S.,Ghaem-Maghami, Ghobad,Mallard, Angela S.,Harutunian, Vahak,et al.
, p. 1901 - 1930 (2007/10/02)
Chloroformate derived Reissert compounds of isoquinoline and of phenanthridine on treatment with base undergo cyclisation with isothiocyanates to give in good yields corresponding imidazoisoquinoline and imidazophenanthroline derivatives.Phthalazine Reissert compound analogues give open chain adducts under the same conditions which can be cyclised to derivatives of the novel imidazophthalazine system by heating in the presence of molecular sieves.When carbon disulphide is the heterocumulene cyclisation is not observed but open chain dithio-ester derivatives can be isolated on alkylation of the intermediate sodium salts.
