22509-51-9Relevant articles and documents
Electrodimerization ofN-Alkoxyamides for the Synthesis of Hydrazines
Nasier, Abudulajiang,Chang, Xihao,Guo, Chang
, p. 16068 - 16076 (2021/09/18)
An efficient and valuable N-N dimerization reaction ofN-alkoxyamides is reported under undivided electrolytic conditions. This electrochemical strategy provides a powerful way to access a wide range of advanced, highly functionalized hydrazines. Remarkably, anN-centered radical generated from the cleavage of the N-H bond under electrolytic conditions plays a crucial role in this transformation. Furthermore, variousN-alkoxyamides bearing different substituents are suitable in this transformation, furnishing the corresponding hydrazines in up to 92% yield.
Rhodium(III)-catalyzed chemodivergent annulations between: N-methoxybenzamides and sulfoxonium ylides via C-H activation
Xu, Youwei,Zheng, Guangfan,Yang, Xifa,Li, Xingwei
supporting information, p. 670 - 673 (2018/01/28)
Chemodivergent and redox-neutral annulations between N-methoxybenzamides and sulfoxonium ylides have been realized via Rh(iii)-catalyzed C-H activation. The sulfoxonium ylide acts as a carbene precursor, and coupling occurs under acid-controlled condition
Propargyl Alcohols as One-Carbon Synthons: Redox-Neutral Rhodium(III)-Catalyzed C-H Bond Activation for the Synthesis of Isoindolinones Bearing a Quaternary Carbon
Wu, Xiaowei,Wang, Bao,Zhou, Yu,Liu, Hong
supporting information, p. 1294 - 1297 (2017/03/23)
Herein, rhodium(III)-catalyzed C-H activation/subsequent [4 + 1] cyclization reactions between benzamides and propargyl alcohols are reported in which propargyl alcohols serve as unusual one-carbon units. This title transformation led to a series of isoin
Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones
Sharma, Nidhi,Saha, Rajib,Parveen, Naziya,Sekar, Govindasamy
supporting information, p. 1947 - 1958 (2017/06/09)
A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).
New heteroannulation reactions of N-Alkoxybenzamides by Pd(II) Catalyzed C-H activation
Wrigglesworth, Joe W.,Cox, Brian,Lloyd-Jones, Guy C.,Booker-Milburn, Kevin I.
supporting information; experimental part, p. 5326 - 5329 (2011/12/01)
A new palladium(II) catalyzed methodology for the direct synthesis of alkylidene isoindolinones from N-alkoxybenzamides is presented. Isoindolinone formation proceeds through a highly efficient and E-selective C-H activation/Heck/Aza-Wacker sequence. Subs
N-[(diphenoxyphosphoryl)oxy]-2-phenyl-1H-benzimidazole as a versatile reagent for synthesis O-alkylhydroxamic acids
Kokare, Nagnnath D.,Shinde, Devanand B.
, p. 981 - 986 (2008/09/21)
(Chemical Equation Presented) Highly efficient reagent, N-[(diphenoxyphosphoryl)oxy]-2-phenyl-1H-benzimidazole was synthesized and its applicability was demonstrated for the synthesis of O-alkyl hydroxamic acids. The efficiency of the reagent was evaluate
Design, synthesis and utilization of a novel coupling reagent for the preparation of O-alkyl hydroxamic acids
Kokare, Nagnnath D.,Nagawade, Rahul R.,Rane, Vipul P.,Shinde, Devanand B.
, p. 4437 - 4440 (2008/02/03)
An efficient novel reagent, phosphoric acid diethyl ester 2-phenyl-benzimidazol-1-yl ester, was designed, and synthesized and its applicability was demonstrated for the preparation of O-alkyl hydroxamic acids. The O-alkyl hydroxamic acids of N-protected a
Efficient Conversions of Carboxylic Acids into O-Alkyl, N-Alkyl and O,N-Dialkylhydroxamic Acids
Katritzky, Alan R.,Kirichenko, Nataliya,Rogovoy, Boris V.
, p. 2777 - 2780 (2007/10/03)
Carboxylic acids were conveniently converted into unsubstituted, N-alkyl-, O-alkyl-, and O,N-dialkylhydroxamic acids via acylbenzotriazole intermediates. The ready availability of the reagents, mild conditions, and easy handling of the intermediates are advantageous.
HERON rearrangement of N,N'-diacyl-N,N'-dialkoxyhydrazines a - Theoretical and experimental study
Glover, Stephen A.,Guoning, Mo,Rauk, Arvi
, p. 3413 - 3426 (2007/10/03)
Ab initio calculations at the B3LYP/6-31G* level on N-methoxy-N- dimethylaminoformamide and its rearrangement to methyl formate and 1,1- dimethyldiazene through the HERON reaction, have been carded out in conjunction with an experimental study of the HERON reactions of N,N'- diacyl-N,N'-dialkoxyhydrazines. Substituent effects are in accord with the theoretical properties of the transition state and point to an anomerically driven process in which donor groups on the anomeric nitrogen and withdrawing groups on the migrating alkoxy oxygen facilitate the rearrangement process.
Evidence for the Formation of Nitrenium Ions in the Acid-catalysed Solvolysis of Mutagenic N-Acetoxy-N-Alkoxybenzamides
Campbell, John J.,Glover, Stephen A.,Hammond, Gerard P.,Rowbottom, Colleen A.
, p. 2067 - 2080 (2007/10/02)
In aqueous acetonitrile, N-acetoxy-N-alkoxybenzamides undergo acid-catalysed solvolysis by the AAl1 mechanism to give acetic acid and nitrenium ions.This is indicated by an inverse dependence of the acid-independent rate constant, kH, upon the activity of water, a solvent kinetic isotope effect of 0.44 and positive Σ(excit.) values.In addition, relief of steric compression at the nitrogen enhances the rate of solvolysis.Hammett correlations with ?+ substituent constants were found for the rates of solvolysis of para-substituted-N-acetoxy-N-butoxybenzamides and N-acetoxy-N-(para-substituted benzyloxy) benzamides.This fact and the low ρ-values of -1.35 and -1.56, respectively, are indicative of a strong build-up of positive charge in the transition state which has both nitrenium ion and oxonium ion character and is in accordance with computed molecular-orbital properties of N-alkoxynitrenium ions.Greater levels of mutagenicity have been measured for those compounds which are more readily solvolysed to nitrenium ions.
