Autotandem Catalyst: From Acylhydrazones to N′,N′-Methylaliphatic Acylhydrazides via Transfer Hydrogenation/N-Methylation with Methanol Catalyzed by a Cp* Iridium Complex Bearing a Functional Ligand

Article

Author: Li, Feng ; Luo, Shiyuan ; Yang, Xiaoguang ; Xu, Xiangchao ; Shi, Qixun ; Zhang, Peng

A new strategy for the synthesis of N',N'-methylaliphatic acylhydrazides from acylhydrazones via transfer hydrogenation/N-methylation with methanol as both the hydrogen source and the methylating reagent has been proposed and accomplished. In the presence of [Cp*Ir(2,2'-bpyO)(H₂O)] (1 mol %) and Cs₂CO₃ (0.3 equiv), a range of desired products were obtained in high yields. It was also confirmed that functional units in the bpy ligand of the catalyst are crucial for the catalytic activity of iridium complexes. The mechanistic investigation and practical application of the present catalytic system were also presented.

01 Oct 2022·Applied Organometallic Chemistry

Arene Ru (II)‐catalyzed facile synthesis of N‐acylhydrazones via acceptorless dehydrogenative coupling strategy

Author: Pennamuthiriyan, Anandaraj ; Sémeril, David ; Sundar, Saranya ; Rengan, Ramesh

A facile catalytic one‐pot synthesis of N‐acylhydrazones via acceptorless dehydrogenative coupling of readily available alcohols and benzohydrazides (R2CONHNH2) using arene ruthenium (II) complexes has been described. The coupling of alcohols with various benzohydrazides using ruthenium catalysts provide a wide range of N‐acylhydrazones in good to excellent yields (63–93%; 32 examples). The present protocol offers high selectivity of hydrazones without any alkylated products and tolerates a range of functional groups. Control experiments indicate that the mechanism proceeds via acceptorless dehydrogenation of alcohols, and hydrogen and water are the sole by‐products. The gram scale synthesis illustrates the usefulness of the present strategy.

01 Oct 2014·European Journal of Organic Chemistry

Mild, Stereoselective, and Highly Efficient Synthesis of N‐Acylhydrazones Mediated by CeCl₃·7H₂O in a Broad Range of Solvents

Author: dos Santos Filho, Jose Mauricio

AbstractIn a mild and practical approach, hydrazides and aldehydes underwent condensation reactions that were mediated by cerium(III) chloride to be rapidly converted into N‐acylhydrazones. This method uses a minimal catalytic amount of cerium(III), is stereoselective, and offers several unique features, such as compatibility with aryl, heterocyclic, alkenyl, and sensitive functional groups as well as the ability to prepare N‐acylhydrazones from highly hindered substrates. More strikingly, cerium(III) efficiently mediated the reaction with less reactive substrates such as diaryl and alkyl aryl ketones, when classical protocols without the catalyst were not effective. This method enables the synthesis of a structurally diverse library of N‐acylhydrazones that have applications in synthetic and medicinal chemistry.

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Indication	Highest Phase	Country/Location	Organization	Date
Analgesia	Preclinical	Brazil	Federal University of Rio de Janeiro	01 Sep 2009

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