5580-33-6Relevant academic research and scientific papers
Efficient nitriding reagent and application thereof
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Paragraph 0337-0340, (2021/03/31)
The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
supporting information, p. 281 - 285 (2020/01/28)
The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
Efficient Hydration of Nitriles Promoted by Gallic Acid Derived from Renewable Bioresources
Deng, Tao,Wang, Cheng-Zhang
, p. 1349 - 1353 (2017/04/14)
An efficient gallic acid promoted nitriles hydration at room temperature with ethanol/water as a solvent has been developed. The present protocol offers a wide range of amides in moderate to good yields. Moreover, galla chinensis extract can serve as the promoter to perform the hydration, which also shows the potential utilization of natural feedstocks.
A Convenient Palladium-Catalyzed Aminocarbonylation of Aryl Iodides to Primary Amides under Gas-Free Conditions
Qi, Xinxin,Ai, Han-Jun,Cai, Chuang-Xu,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
supporting information, p. 7222 - 7225 (2018/01/02)
A convenient procedure for the synthesis of aromatic primary amides through palladium-catalyzed aminocarbonylation of aryl iodides has been developed. With ammonium hydrogen carbonate as the solid nitrogen source and formic acid as the liquid CO source, a variety of primary amides were obtained in moderate to excellent yields under gas-free conditions.
Synthesis of primary amides by aminocarbonylation of aryl/hetero halides using non-gaseous NH3 and CO sources
Suresh,Baburajan, Poongavanam,Ahmed, Mansur
supporting information, p. 4864 - 4867 (2015/07/28)
Abstract A practically simple method for the synthesis of primary amides via the palladium-catalysed aminocarbonylation of aromatic halides by using solid sources of gaseous ammonia and carbon monoxide is described. The system tolerated a wide variety of hindered and functionalized aryl/hetero halides and afforded good to excellent yields (69-94%) of the amide. Pharmacologically active Exalamide and Pyrazinecarboxamide were synthesised in high yields to demonstrate the effectiveness of this method.
Copper-catalyzed aerobic oxidative C-C bond cleavage for C-N bond formation: From ketones to amides
Tang, Conghui,Jiao, Ning
supporting information, p. 6528 - 6532 (2014/06/24)
A novel copper-catalyzed aerobic oxidative C(CO)-C(alkyl) bond cleavage reaction of aryl alkyl ketones for C-N bond formation is described. A series of acetophenone derivatives as well as more challenging aryl ketones with long-chain alkyl substituents could be selectively cleaved and converted into the corresponding amides, which are frequently found in biologically active compounds and pharmaceuticals.
Benzamide synthesis by direct electrophilic aromatic substitution with cyanoguanidine
Naredla, Rajasekhar Reddy,Klumpp, Douglas A.
experimental part, p. 4779 - 4781 (2012/09/07)
Cyanoguanidine is an inexpensive commodity chemical and it is found to be a useful reagent for the direct Friedel-Crafts carboxamidation of arenes. The reaction works best in an excess of Bronsted superacid, an observation suggesting the involvement of a superelectrophilic intermediate. Theoretical calculations indicate that the most stable diprotonated species involves protonation at the guanidine and cyano nitrogen atoms.
One-pot synthesis of symmetrical 1,3-diarylureas or substituted benzamides directly from benzylic primary alcohols and effective oxidation of secondary alcohols to ketones using phenyliodine diacetate in combination with sodium azide
Li, Xiao-Qiang,Wang, Wei-Kun,Han, Yi-Xin,Zhang, Chi
experimental part, p. 2588 - 2598 (2010/12/25)
Benzylic primary alcohols can be directly converted into symmetrical 1,3-diarylureas or substituted benzamides via an one-pot oxidative reaction using the combined reagent of phenyliodine diacetate and sodium azide. This new reaction constitutes a step-economical way to prepare symmetric 1,3-diarylureas or substituted benzamides depending upon the substituents on the phenyl rings of starting alcohols. The sodium acetate generated in situ from the ligand exchange between phenyliodine diacetate and sodium azide plays the pivotal role in the formation of 1,3-diarylureas. In addition, it is also found that various secondary alcohols can be readily oxidized to their corresponding ketones in excellent yields using the same reagent system of phenyliodine diacetate and sodium azide. Generally, secondary alcohols are preferentially oxidized to the corresponding ketones in the presence of primary ones with the limited amounts of phenyliodine diacetate and sodium azide.
