6233-05-2Relevant articles and documents
Nitrene-mediated intermolecular N–N coupling for efficient synthesis of hydrazides
Wang, Hao,Jung, Hoimin,Song, Fangfang,Zhu, Shiyang,Bai, Ziqian,Chen, Danye,He, Gang,Chang, Sukbok,Chen, Gong
, p. 378 - 385 (2021/03/31)
N–N linkages are found in many natural compounds and endow fascinating structural and functional properties. In comparison to the myriad methods for the construction of C–N bonds, chemistry for N–N coupling, especially in an intermolecular fashion, remains underdeveloped. Here, we report a nitrene-mediated intermolecular N–N coupling of dioxazolones and arylamines under iridium or iron catalysis. These reactions offer a simple and efficient method for the synthesis of various hydrazides from readily available carboxylic acid and amine precursors. Although the Ir-catalysed conditions usually give higher N–N coupling yield than the Fe-catalysed conditions, the reactions of sterically more demanding dioxazolones derived from α-substituted carboxylic acids work much better under the Fe-catalysed conditions. Mechanistic studies revealed that the nitrogen atom of Ir acyl nitrene intermediates has strong electrophilicity and can undergo nucleophilic attack with arylamines with the assistance of Cl···HN hydrogen bonding to form the N–N bond with high efficiency and chemoselectivity. [Figure not available: see fulltext.].
Synthesis method for intermolecular N-N bonding and corresponding synthesized compound
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Paragraph 0030-0032; 0033-0037; 0045-0046; 0058; 0063, (2021/07/24)
The invention relates to a synthesis method for intermolecular N-N bonding and a corresponding compound. According to the invention, the direct insertion reaction of N-H bonds by nitrene is completed, and a brand-new N-N coupling reaction method is developed. The reaction uses a nitrene precursor, under the action of a catalyst, an intermolecular direct N-N coupling reaction of the nitrene precursor and an amine compound can be realized, and a tetra-substituted hydrazine compound is constructed in one step.
Copper(ii)-catalyzed coupling reaction: An efficient and regioselective approach to N′,N′-diaryl acylhydrazines
Zhang, Ji-Quan,Huang, Gong-Bin,Weng, Jiang,Lu, Gui,Chan, Albert S. C.
, p. 2055 - 2063 (2015/03/05)
Using N′-aryl acylhydrazines as aryl donors, a novel copper(ii)-catalyzed homo-coupling reaction of N′-aryl acylhydrazines has been developed for the synthesis of N′,N′-diaryl acylhydrazines. We also provided a complementary procedure for the preparation of unsymmetrical diaryl acylhydrazines via cross-coupling reaction. These protocols featured mild reaction conditions, wide functional group tolerance and highly regioselective products. Control experiments indicated that this kind of coupling reaction might undergo a transient acyl diazene intermediate. This journal is
Rh(iii)-catalyzed synthesis of 1-aminoindole derivatives from 2-acetyl-1-arylhydrazines and diazo compounds in water
Liang, Yujie,Yu, Ke,Li, Bin,Xu, Shansheng,Song, Haibin,Wang, Baiquan
supporting information, p. 6130 - 6133 (2014/06/09)
A novel and direct approach to synthesize 1-aminoindole derivatives by Rh(iii)-catalyzed cyclization of 2-acetyl-1-arylhydrazines with diazo compounds via aryl C-H activation has been developed. This intermolecular annulation involving tandem C-H activati
Rh(III)-catalyzed oxidative coupling of 1,2-disubstituted arylhydrazines and olefins: A new strategy for 2,3-dihydro-1H-indazoles
Han, Sangil,Shin, Youngmi,Sharma, Satyasheel,Mishra, Neeraj Kumar,Park, Jihye,Kim, Mirim,Kim, Minyoung,Jang, Jinbong,Kim, In Su
supporting information, p. 2494 - 2497 (2014/05/20)
A rhodium(III)-catalyzed oxidative olefination of 1,2-disubstituted arylhydrazines with alkenes via sp2 C-H bond activation followed by an intramolecular aza-Michael reaction is described. This strategy allows the direct and efficient construct
Reduction of Ag(I) by 1-acyl-2-arylhydrazines: Mechanism of photographic infectious development
Bowman, W. Russell,Forshaw, J. Anthony,Hall, Kevin P.,Kitchin, Jonathan P.,Mott, Andrew W.
, p. 3961 - 3972 (2007/10/03)
The photographic process of 'infectious development' in which 1-acyl-2-arylhydrazines reduce Ag(I) has been studied using analogues. 1-Acyl-2-aryldiazenes, resulting from oxidation of 1-acyl-2-arylhydrazines, are hydrolysed to anions of aryldiazenes (ArN = NH), which undergo further oxidation with loss of nitrogen to yield aryl radicals. The aryl radicals cause 'feedback inhibition' which is prevented by the addition of benzhydrol.
