1215-52-7Relevant articles and documents
A convenient way for alkylation of amines using xanthate esters
Sukrutha, Kodipura P.,Swaroop, Toreshettahally R.,Preetham, Ramesh,Lokanath, Neratur K.,Rangappa, Kanchugarakoppal S.,Sadashiva, Maralinganadoddi P.
, p. 2316 - 2323 (2021/06/14)
N-alkylation of amines by the reaction with xanthate esters in the presence of acetic acid catalyst in ethanol is reported. Short reaction time, high yield, general applicability and environmentally benign nature are the noteworthy features of our protocol. The probable mechanism for the formation N-alkylation of amines is proposed.
Synthesis of 3 H-1,2,4-Triazol-3-ones via NiCl2-Promoted Cascade Annulation of Hydrazonoyl Chlorides and Sodium Cyanate
Du, Shiying,Yang, Zuguang,Tang, Jianhua,Chen, Zhengkai,Wu, Xiao-Feng
supporting information, p. 2359 - 2363 (2021/04/05)
A nickel-promoted cascade annulation reaction for the facile synthesis of 3H-1,2,4-triazol-3-ones from readily available hydrazonoyl chlorides and sodium cyanate has been developed. The transformation occurs through a cascade nickel-promoted intermolecular nucleophilic addition-elimination process, intramolecular nucleophilic addition, and a hydrogen-transfer sequence. The method has been successfully applied for the construction of the core skeleton of the angiotensin II antagonist.
Nickel-Catalyzed N-Alkylation of Acylhydrazines and Arylamines Using Alcohols and Enantioselective Examples
Yang, Peng,Zhang, Caili,Ma, Yu,Zhang, Caiyun,Li, Aijie,Tang, Bo,Zhou, Jianrong Steve
supporting information, p. 14702 - 14706 (2017/10/20)
A borrowing-hydrogen reaction between amines and alcohols is an atom-economic way to prepare alkylamines, ideally with water as the sole byproduct. Herein, nickel catalysts are used for direct N-alkylation of hydrazides and arylamines using racemic alcohols. Moreover, a nickel catalyst of (S)-binapine was used for an asymmetric N-alkylation of benzohydrazide with racemic benzylic alcohols.
Method for preparing secondary amine or N'-alkyl hydrazide through nickel catalysis N-alkylation reaction
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Paragraph 0104; 0105; 0106; 0107; 0108, (2017/12/27)
The invention discloses a method for preparing secondary amine or N'-alkyl hydrazide through nickel catalysis N-alkylation reaction. Amine or hydrazide is used as raw materials; alcohol is used as an alkylation agent; N-alkylation reaction is performed under the nickel catalysis condition; the secondary amine or N'-alkyl hydrazide is prepared. Compared with the prior art, the method provided by the invention has the advantages that the N-alkylation reaction is performed; active catalysts can be generated in situ by nickel salt and phosphine ligands; the preparation of catalysts in advance is avoided; the operation is simple and convenient; the experiment steps and the experiment cost are reduced. Cheap nickel is used as the catalysts; the consumption of the catalysts is low; the use of expensive and high-toxicity precious metal is avoided; the experiment cost is further reduced; the hydrogen borrowing strategy is utilized; the N'-alkylation of the hydrazide is realized for the first time; byproducts only contain water. Compared with other preparation methods, the method has the advantage that the reaction environment-friendly performance is realized.
Metal-Free Synthesis of 1,3,4-Oxadiazoles from N′-(Arylmethyl)hydrazides or 1-(Arylmethyl)-2-(arylmethylene)hydrazines
Shang, Zhenhua,Chu, Qianqian,Tan, Sheng
, p. 1032 - 1040 (2015/03/30)
An efficient and versatile metal-free synthesis of 1,3,4-oxadiazoles from N′-(arylmethyl)hydrazides or 1-(arylmethyl)-2-(arylmethylene)hydrazines through oxidative dehydrogenation is reported. A range of 2,5-disubstituted 1,3,4-oxadiazoles were prepared by treating N′-(arylmethyl)hydrazides with (diacetoxyiodo)benzene in acetonitrile or by treating 1-(arylmethyl)-2-(arylmethylene)hydrazines with [bis(trifluoroacetoxy)iodo]benzene in methyl tert-butyl ether. Aldehyde N-acylhydrazones and aldazines were initially generated in situ as intermediates.
Reductive alkylation of hydrazine derivatives with α-picoline-borane and its applications to the syntheses of useful compounds related to active pharmaceutical ingredients
Kawase, Yasushi,Yamagishi, Takehiro,Kato, Jun-Ya,Kutsuma, Teruo,Kataoka, Tadashi,Iwakuma, Takeo,Yokomatsu, Tsutomu
, p. 455 - 464 (2014/03/21)
An efficient method for the direct reductive alkylation of hydrazine derivatives with α-picoline-borane has been developed to synthesize a variety of N-alkylhydrazine derivatives. This method provided N,N-dialkylhydrazine derivatives and N-monoalkylhydrazine derivatives upon fine-tuning of the substrates and the reagent equivalency in a one-pot manner. The method was applied to the synthesis of active pharmaceutical ingredients of therapeutic drugs such as isocarboxazid.
1-Acyl-2-alkylhydrazines by the Reduction of Acylhydrazones
Pei-Lin-Wu,Peng, Shao-Yu,Magrath, Joe
, p. 435 - 438 (2007/10/02)
1-Acyl-2-alkylhydrazines were easily prepared by the reduction of acylhydrazones with triethylsilane in the presence of trifluoroacetic acid.
Convenient Syntheses of 1-Acyl-2-alkylhydrazines
Okawara, Tadashi,Kanazawa, Yasunori,Yamasaki, Tetsuo,Furukawa, Mitsuru
, p. 183 - 184 (2007/10/02)
1-Acyl-2-alkylhydrazines 7 were prepared from hydroxamic acids 1 and amines 6 using 2-chloro-1-methylpyridinium iodide 2 or p-toluenesulfonyl chloride 3 in 27-68percent yield.
