cas 114-83-0, 1-Acetyl-2-phenylhydrazine | Articles data

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A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles
N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is
Yavari, Issa,Khaledian, Omid
supporting information
p. 9150 - 9153
(2020/10/02)

Synthesis of acetamides via oxidative C–C bond cleavage of ketones catalyzed by Cu-immobilized magnetic nanoparticles
Copper supported on magnetite nanoparticles modified with environmentally friendly ligand tricine was devised for synthesis of acetamides via C–C oxidative cleavage of ketones with amines. The catalyst was characterized using different techniques, including Fourier transform infrared, X-ray diffraction, scannin electron microscopy, vibrating sample magnetometry, thermogravimetric analysis, and energy dispersive x-ray spectroscopy. The protocol showed relatively high yields of acetamide products. Furthermore, the magnetic recovery of the catalyst rendered the overall process fast and efficient. It was used in the reaction for six consecutive cycles with negligible loss of catalytic activity. This research is the first report of application of magnetic nanocatalysts for synthesis of acetamides from ketones of low activity through a C–C bond cleavage strategy.
Yazdani, Elahe,Pazoki, Farzane,Salamatmanesh, Arefe,Nejad, Masoume Jadidi,Miraki, Maryam Kazemi,Heydari, Akbar
(2020/07/27)

The impact of cation structure upon the acidity of triazolium salts in dimethyl sulfoxide
A series of triazolium salts, selected for their varying electronic and steric properties, were prepared and their pKa values were determined in DMSO at 25 °C using the bracketing indicator method. The effect of each systematic structural variation upon the acidity of the triazolium cation has been considered, in particular examining the effects of systematically altering electronic properties, quantified through the use of Hammett σ parameters. The first pKa value for an azolium salt that generates a mesionic carbene is also reported. These new data allow for the selection of appropriate bases for the deprotonation of such triazolium salts and the potential to correlate the pKa values determined herein with the nucleophilicity of the corresponding carbenes.
Konstandaras, Nicholas,Dunn, Michelle H.,Guerry, Max S.,Barnett, Christopher D.,Cole, Marcus L.,Harper, Jason B.
supporting information
p. 66 - 75
(2019/12/26)

A magnetically recoverable copper–salen complex as a nano-catalytic system for amine protection via acetylation using thioacetic acid
A novel copper(II)–salen complex was immobilized on the surface of magnetite nanoparticles using chitosan as a linker. This system exhibits superior catalytic activity in acetyl protection of various amines with thioacetic acid as the acetylating reagent. The method has advantages over others in high selectivity, simple work-up, green reaction medium and the application of an easily recoverable heterogeneous catalyst.
Yazdani, Elahe,Kazemi Miraki, Maryam,Salamatmanesh, Arefe,Azarnia, Jamshid,Azizi, Kobra,Ghandi, Leila,Heydari, Akbar
p. 1775 - 1793
(2019/01/16)

Synthesis method for organic synthesis of intermediate acetyl phenylhydrazine
The invention relates to a synthesis method for organic synthesis of an intermediate acetyl phenylhydrazine. The method mainly includes the steps of: adding 3mol phenylhydrazine into a reaction container and 4-5mol p-iodoacetanilide into a reaction container, performing heating to 90-95DEG C, conducting reflux for 130-150min, lowering temperature to 10-15DEG C, filtering the crystal, conducting washing with a methylamine solution and a dichloromethane solution respectively, performing recrystallization in an ethanol solution, precipitating crystals, conducting filtration, and performing dehydration with a dehydrating agent, thus obtaining the finished product acetyl phenylhydrazine.
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(2018/07/30)

Mild and eco-friendly chemoselective acylation of amines in aqueous medium using a green, superparamagnetic, recoverable nanocatalyst
Copper-grafted guanidine acetic acid-modified magnetite nanoparticles (Fe3O4@GAA-Cu(II)) as a green, superparamagnetic and recoverable nanocatalyst is found to promote quantitative N-acylation of various amines in a very short time with an equimolar amount of thioacetic acid in water at room temperature. This method is found to be highly selective for amines and not sensitive to other functional groups. Mild reaction condition, high selectivity, efficiency, simple workup and excellent yields are some of the major advantages of the procedure.
Miraki, Maryam Kazemi,Yazdani, Elahe,Ghandi, Leila,Azizi, Kobra,Heydari, Akbar
(2017/09/30)

Palladium/copper-catalyzed arylation of alkenes with N′-acyl arylhydrazines
A novel ligand-free palladium/copper-catalyzed Heck-type coupling reaction of alkenes and N′-acyl arylhydrazines has been developed by using air as the terminal oxidant. This protocol features wide functional group tolerance and produces highly chemoselective and regioselective products with good to excellent yields.
Zhang, Ji-Quan,Cao, Jun,Li, Wei,Li, Shu-Min,Li, Yong-Kang,Wang, Jian-Ta,Tang, Lei
supporting information
p. 437 - 441
(2017/02/05)

[3+3]-cycloaddition of donor-acceptor cyclopropanes with nitrile imines generated in situ: Access to tetrahydropyridazines
Donor-acceptor cyclopropanes are reacted under the influence of a Lewis acid with hydrazonyl chlorides to afford tetrahydropyridazines. Formally, this transformation can be regarded as a [3 + 3]-cycloaddition of three-membered rings and nitrile imines generated in situ. This efficient method provides fast access to a variety of structurally diverse pyridazine derivatives. The structure of a typical product was confirmed by X-ray crystallography.
Garve, Lennart K. B.,Petzold, Martin,Jones, Peter G.,Werz, Daniel B.
supporting information
p. 564 - 567
(2016/02/18)

Copper(ii)-catalyzed coupling reaction: An efficient and regioselective approach to N′,N′-diaryl acylhydrazines
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
Zhang, Ji-Quan,Huang, Gong-Bin,Weng, Jiang,Lu, Gui,Chan, Albert S. C.
supporting information
p. 2055 - 2063
(2015/03/05)

Microwave-assisted catalyst-free synthesis of substituted 1,2,4-triazoles
A simple, efficient, and mild method has been developed for the synthesis of substituted 1,2,4-triazoles from hydrazines and formamide under microwave irradiation. The reaction proceeds smoothly in the absence of a catalyst and shows excellent functional-group tolerance.
Shelke, Ganesh M.,Rao, V. Kameswara,Jha, Mukund,Cameron, T. Stan,Kumar, Anil
p. 404 - 407
(2015/02/19)

Synthesis of 2,3-dihydro-1H-indazoles by Rh(iii)-catalyzed C-H cleavage of arylhydrazines
A rhodium-catalyzed efficient method for the synthesis of 2,3-dihydro-1H-indazoles is described. The reaction of arylhydrazines with olefins results in the corresponding 2,3-dihydro 1H-indazoles with exclusive regioselectivity via C-H bond activation. The utility of the methodology is illustrated by a rapid synthesis of 1H-indazoles under mild reaction conditions in half an hour. This journal is the Partner Organisations 2014.
Yao, Jinzhong,Feng, Ruokun,Lin, Cong,Liu, Zhanxiang,Zhang, Yuhong
p. 5469 - 5476
(2014/07/21)

A binuclear Mn(ii) complex as an efficient catalyst for transamidation of carboxamides with amines
A binuclear Mn(ii) complex has been synthesized and characterized by different structural methods. The complex contains two unique oxo-bridged metal centres and has been explored as an excellent catalyst for transamidation of carboxamides with amines under solvent-free conditions.
Singh, Divya Pratap,Allam, Bharat Kumar,Singh, Krishna Nand,Singh, Vinod Prasad
p. 1155 - 1158
(2014/01/06)

Formation of enehydrazine intermediates through coupling of phenylhydrazines with vinyl halides: Entry into the Fischer indole synthesis
Cut to the chase: Direct formation of an enehydrazine, an intermediate in the classic Fischer indole synthesis, solves the regioselectivity problem associated with indolization. This approach not only achieves selective synthesis of indoles through proper selection of the vinyl halide, but also leads to quick construction of desoxyeseroline and esermethole, as well as the key structural motif in the Akuammiline alkaloid vincorine. Copyright
Zhan, Fuxu,Liang, Guangxin
supporting information
p. 1266 - 1269
(2013/03/13)

Indole synthesis by rhodium(III)-catalyzed hydrazine-directed C-H activation: Redox-neutral and traceless by N-N bond cleavage
Fishing for complements! There is an alternative to the useful Fischer indole synthesis. The new method utilizes the same retrosynthetic disconnection but is based on a RhIII-catalyzed directed C-H activation step and a successive coupling with alkynes. Copyright
Zhao, Dongbing,Shi, Zhuangzhi,Glorius, Frank
supporting information
p. 12426 - 12429
(2013/12/04)

Hypervalent iodine catalyzed transamidation of carboxamides with amines
This protocol describes the catalytic use of diacetoxyiodobenzene (DIB) for the efficient transamidation of carboxamides with amines under mild conditions.
Vanjari, Rajeshwer,Kumar Allam, Bharat,Nand Singh, Krishna
p. 1691 - 1694
(2013/03/28)

A novel and simple transamidation of carboxamides in 1,4-dioxane without a catalyst
An easy acylation and formylation of amines has been achieved via transamidation using 1,4-dioxane. The investigation works efficiently without an added catalyst and completes within short time under microwave irradiation.
Vanjari, Rajeshwer,Allam, Bharat Kumar,Singh, Krishna Nand
p. 2553 - 2555
(2013/06/05)

Preparation of chiral 1,2,4-triazolium salts as new NHC precatalysts
The preparation of new chiral N,N′-disubstituted 1,2,4-triazolium based NHC salt precursors, Ia′ and Ib, from phenylhydrazine and l-phenylalanine is reported. The 1,3,4-trisubstituted triazolium salt Ia′ was obtained by a stepwise ring construction from l-phenylalanine via the corresponding imino ether and acetohydrazonamide, while a heterocyclic O-/N-heteroatom exchange strategy, based on a ring-opening/ring-closure of the oxadiazolium precursor, afforded the 1,4-disubstituted 1,2,4-triazolium salt Ib. The need for two different synthetic strategies is discussed.
Strand, Ragnhild B.,Solvang, Tina,Sperger, Christian A.,Fiksdahl, Anne
experimental part
p. 838 - 842
(2012/09/22)

Use of acylhydrazine- and acylhydrazone-type ligands to promote CuI-catalyzed C-N cross-coupling reactions of aryl bromides with N-heterocycles
A series of ten acylhydrazine- and acylhydrazone-type ligands were designed and synthesized. Their electronic and steric properties were easily modified and tuned by varying the substituents in the vicinity of the acylhydrazine and acylhydrazone units. The effect of ligands on the catalytic activity of Ullmann reactions was assessed by using a combination of these ligands with CuI. The catalytic system is very efficient for the C-N coupling reaction of azoles with aryl and heteroaryl bromides. A simple and efficient procedure for copper-catalyzed C-N cross-coupling reactions between aryl bromides and NH-containingheterocycles is illustrated. Readily available acylhydrazine- and acylhydrazone-typeligands promote the reaction.
Li, Liuyi,Zhu, Lei,Chen, Dagui,Hu, Xuelei,Wang, Ruihu
supporting information; experimental part
p. 2692 - 2696
(2011/06/25)

Reduction of hydrazines to amines with aqueous solution of titanium(iii) trichloride
N-N bond cleavage in hydrazines is widely used in the preparation of amines and thus occupies a significant place in organic synthesis. In this paper, we report a new method for the reductive cleavage of N-N bonds in hydrazines by commercially available and cheap aqueous titanium(iii) trichloride. The reaction proceeds smoothly under a broad pH range from acidic to neutral and basic conditions to afford amines in good yields. This method is compatible with substrates containing functionalities such as C-C double bonds, benzyl-nitrogen bonds, benzyloxy and acyl groups. The Royal Society of Chemistry 2011.
Zhang, Yan,Tang, Qiang,Luo, Meiming
supporting information; experimental part
p. 4977 - 4982
(2011/08/05)

Additive-free chemoselective acylation of amines
Aliphatic and aromatic amines are efficiently acylated by acetic, pivalic, benzoic, phthalic, or maleic anhydrides in ethyl acetate at room temperature. Under the same experimental conditions, amino alcohols are chemoselectively acylated at the amino group.
Temperini, Andrea,Terlizzi, Raffaella,Testaferri, Lorenzo,Tiecco, Marcello
experimental part
p. 295 - 302
(2010/03/30)

Synthesis of indoles via alkylidenation of acyl hydrazides
Indoles have been synthesised via alkylidenation of acyl phenylhydrazides using phosphoranes and the Petasis reagent, followed by in situ thermal rearrangement of the product enehydrazines. The Petasis reagent provides an essentially neutral equivalent of the [acid-catalysed] Fischer indole synthesis, but with acyl phenylhydrazides as starting substrates. Alkylidene triphenylphosphoranes convert aroyl phenylhydrazides to indoles, but acyl phenylhydrazides derived from aliphatic carboxylic acids undergo a Brunner reaction to form indolin-2-ones.
Hisler, Kevin,Commeureuc, Aurélien G.J.,Zhou, Sheng-ze,Murphy, John A.
supporting information; experimental part
p. 3290 - 3293
(2009/08/17)

The enantioselective benzoin condensation promoted by chiral triazolium precatalysts: Stereochemical control via hydrogen bonding
The design of a new class of triazolium ion precatalysts incorporating protic substituents is described. These materials promote the enantioselective benzoin condensation of a range of aromatic aldehydes (1-62% ee). Catalyst evaluation studies strongly support the involvement of hydrogen bond donation by the catalyst in the stereocentre-forming step of the catalytic cycle.
O'Toole, Sarah E.,Connon, Stephen J.
experimental part
p. 3584 - 3593
(2010/01/06)

Acyl maleic hydrazides as versatile acyl transferring agents
Acyl maleic hydrazides have been found to act as effective acyl transferring agents to substrates containing heteroatom nucleophiles such as amines, phenols, alcohols and thiols under mild and convenient conditions.
Mashraqui, Sabir H.,Shivaji, Jadhav L.
p. 121 - 123
(2007/10/03)

Ac2O-Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation
Acetic anhydride-pyridine over basic alumina has been used in order to carry out acetylations of hydroxy, thiol and amino groups in solvent-free conditions under microwave irradiation. The technique can be extended for selective acetylations by regulation of irradiation time.
Paul, Satya,Nanda, Puja,Gupta, Rajive,Loupy, André
p. 4261 - 4265
(2007/10/03)

Reaction of β-cyanomethylene-β-enamino diketones and -keto esters with hydrazines: Synthesis of pyrazole and pyridine derivatives
4-Acetyl-3-amino-5-oxo-3-hexenenitrile (1a) reacts with hydrazines to give pyrazolyl enaminonitriles (2) while 2-acetyl-3-amino-4-cyano-2-butenoic acid methyl ester (1b) reacts with hydrazines to give pyridine derivatives (6) or (7).
Vicentini, Chiara B.,Manfrini, Maurizio,Mazzanti, Manuela,Veronese, Augusto C.
p. 791 - 798
(2007/10/03)

Preparation, properties, and reductive alkylation of arylhydrazides
1 [-Acy]-2-arylhydrazines (1), readily obtained in high yield from the condensation of arylhydrazines and the appropriate liquid carboxylic acid (2), underwent reductive alkylation with the same or different liquid carboxylic acids (2) and NaBH4 to give 1-acyl-2-alkyl-2-arylhydrazines (3) in good to moderate yields. The carboxylic acid has both the role of supplying the entering alkyl group and of acting as solvent. Most likely, it also modifies the BH4- anion to an active reducing agent under those conditions. The 1H NMR criteria for identifying the location of acylation of hydrazines and E and Z isomers are given. The MS spectra of the prepared hydrazides were analyzed in order to identify relevant structural features leading to specific fragmentations.
Verardo, Giancarlo,Toniutti, Nicoletta,Giumanini, Angelo G.
p. 1180 - 1187
(2007/10/03)

Study of the reaction of 2-acyl 1,3-dicarbonyl compounds with hydrazines by 1H NMR spectroscopy
The reaction of 2-acyl 1,3-dicarbonyl compounds with hydrazine and phenylhydrazine was studied by 1H NMR spectroscopy.It was shown that the formation of functionally 4-substituted pyrazoles is promoted if the reaction is conducted in protic solvents at reduced temperature.The presence of the benzoyl groups in the 2-acyl 1,3-dicarbonyl compounds leads to the preferential formation of the cleavage products, i.e., the corresponding acylhydrazines and 1,3-dicarbonyl compounds.It was established that the initial reaction product is consumed in two directions, i.e., cyclization with the formation of functionally 4-substituted pyyrazoles and cleavage with the formation of acetylhydrazines and the corresponding 1,3-dicarbonyl compounds.
Emelina, E. E.,Ershov, B. A.,Zelenin, A. K.,Selivanov, S. I.
p. 1630 - 1636
(2007/10/03)

Addition of Semidione Radicals to Arenediazonium Ions: Synthesis of 1,1-Diacyl-2-arylhydrazines
The α-dicarbonyl compounds 1 are selectively reduced to semidione radicals 2 by aqueous Ti3+, via inner-sphere electron transfer (ET).When an equimolar amount of an arenediazonium salt (3) is present, 2 adds to the nitrogen-nitrogen triple bond of 3 to afford the intermediate azo radical cation C, which, depending on the nature of the para substituent of the N-phenyl ring, undergoes rearrangement to a 1,1-diacyl-2-arylhydrazine (4) or preferentially reduction to a hydrazone (5).A mechanism that accounts for both the rearrangement and the substituent effects that are observed is proposed.
Clerici, Angelo,Porta, Ombretta
p. 6813 - 6818
(2007/10/02)

1,1,1-TRICHLOROPROPANONE: A MILD, SELECTIVE ACETYLATING AGENT
The use of the title compound in the acetylation of primary and secondary amines is described.
Salim, Jose Roberto,Nome, Faruk,Rezende, Marcos Caroli
p. 1181 - 1188
(2007/10/02)

2-ACETYL-SUBSTITUTED POLYFLUORINATED β-KETO ESTERS IN REACTION WITH AMINES
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Pashkevich, K. I.,Krokhalev, V. M.,Saloutin, V. I.
p. 1202 - 1206
(2007/10/02)

New routes to 1,2-diazetidin-3-ones
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Taylor,Hinkle
p. 4107 - 4110
(2007/10/02)

PREPARATION OF HYDRAZIDES USING SILICON TETRACHLORIDE AS COUPLING AGENT
Silicon tetrachloride proved to be an effective reagent for the preparation of hydrazides from carboxylic acids.Yields were comparable to those obtained via N,N'-dicyclohexylcarbodiimide (DCC) and the procedure was used to synthesize some hydrazides which are difficult to obtain otherwise.
Kornet, Milton J.,Tita, Terence T.,Thio, Alan P.
p. 1261 - 1274
(2007/10/02)

SYNTHESIS AND SOME PROPERTIES OF 2-IMINO-Δ4-1,3,4,2λ5-OXADIAZAPHOSPHOLINES
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Razhabov, A.,Yusupov, M. M.
p. 667 - 669
(2007/10/02)

REACTION OF 2-ARYLAZO-2,5-DIMETHYL-3(2H)-FURANONES WITH AMMONIA. PREPARATION OF β-ACETYL-β-(3-AMINO-2-BUTENOYL)ARYLHYDRAZINES.
Ring opening of 2-arylazo-2,5-dimethyl-3(2H)-furanones (1a-d) with ammonia leads to previously unknown β-acetyl-β-(3-amino-2-butenoyl)arylhydrazines (3a-d).The reaction mechanism is discussed.
Venturello, Carlo,D'Aloisio, Rino
p. 2895 - 2898
(2007/10/02)