40887-05-6Relevant academic research and scientific papers
Mild and efficient synthesis of carbazates and dithiocarbazates via a three-component coupling using Cs2CO3 and TBAI
Fox, Daniel L.,Ruxer, John T.,Oliver, John M.,Alford, Kasey L.,Salvatore, Ralph Nicholas
, p. 401 - 405 (2004)
Efficient methods for the synthesis of carbazates and dithiocarbazates have been developed. In the presence of cesium carbonate (Cs2CO 3) and tetrabutylammonium iodide (TBAI) a hydrazine, CO2 or CS2, and an alkyl halide underwent a three-component coupling at room temperature. Various unprotected hydrazines and alkyl halides were examined and the results demonstrated this methodology was highly chemoselective. Applications toward the synthesis of azadepsipeptides and other pseudopeptides are described.
Hydrogen peroxide based oxidation of hydrazines using HBr catalyst
Du, Wanting,Ma, Zichao,Shao, Liming,Wang, Jian
, (2021/11/18)
Azo compounds (RN = NR′) are an important class of organic molecules that find wide application in organic synthesis. Herein, we report an efficient, practical and metal-free oxidation of hydrazines (RNH-NHR’) to azo compounds using 5 mol% HBr and hydrogen peroxide as terminal oxidant. This new method has been demonstrated by 40 examples with excellent yields. In addition, we showcased two examples of the one-pot sequential reactions involving our hydrazine oxidation/hydrolysis/Heck reaction or Cu-catalyzed N-arylation with aryl boronic acid. The distinct advantages of this protocol include metal-free catalysis, waste prevention, and easy operation.
Electrochemical dehydrogenation of hydrazines to azo compounds
Du, Ke-Si,Huang, Jing-Mei
supporting information, p. 1680 - 1685 (2019/04/08)
A strategy for the electrochemical dehydrogenation of hydrazine compounds is disclosed under ambient conditions. This protocol proceeded smoothly in ethanol by employing electrons as clean oxidants. Its synthetic value is well demonstrated by the highly efficient synthesis of symmetric and unsymmetric azo compounds. It is an environmentally friendly transformation and the present protocol was effective on a large scale.
Aerobic Oxidation of Alkyl 2-Phenylhydrazinecarboxylates Catalyzed by CuCl and DMAP
Kim, Min Hye,Kim, Jinho
, p. 1673 - 1679 (2018/02/09)
Recently, various fruitful organic reactions such as a catalytic Mitsunobu reaction were reported by virtue of alkyl 2-phenylazocarboxylates, however, the synthesis of alkyl 2-phenylazocarboxylates largely depended on the stoichiometric use of toxic oxidants. In this manuscript, an environment-friendly aerobic oxidative transformation of alkyl 2-phenylhydrazinecarboxylates to alkyl 2-phenylazocarboxylates is disclosed. The use of CuCl and DMAP system efficiently catalyzed the aerobic oxidation of alkyl 2-phenylhydrazinecarboxylates under mild conditions. The reaction rate of the present Cu-catalysis was much faster than that of the previously reported Fe-catalysis, and a variety of azo products were synthesized within 3 h. The present protocol was effective on larger scale. It was observed that the produced azo compound could undergo various reactions without isolation through one-pot sequential protocols.
Reduction of hydrazines to amines with aqueous solution of titanium(iii) trichloride
Zhang, Yan,Tang, Qiang,Luo, Meiming
supporting information; experimental part, p. 4977 - 4982 (2011/08/05)
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.
N′,2-Diphenylquinoline-4-carbohydrazide based NK3 receptor antagonists
Elliott, Jason M.,Carling, Robert W.,Chambers, Mark,Chicchi, Gary G.,Hutson, Peter H.,Jones, A. Brian,MacLeod, Angus,Marwood, Rose,Meneses-Lorente, Georgina,Mezzogori, Elena,Murray, Fraser,Rigby, Michael,Royo, Inmaculada,Russell, Michael G.N.,Sohal, Bindi,Tsao, Kwei Lan,Williams, Brian
, p. 5748 - 5751 (2007/10/03)
A new class of potent NK3R antagonists based on the N′,2-diphenylquinoline-4-carbohydrazide core is described. In an ex vivo assay in gerbil, the lead compound 2g occupies receptors within the CNS following oral dosing (Occ90 30 mg/k
QUINOLINE DERIVATIVES AS NEUROKININ RECEPTOR ANTAGONISTS
-
Page/Page column 27, (2008/06/13)
The present invention relates to substituted quinoline-4-carboxylic acid hydrazides defined herein, pharmaceutical compositions comprising them and their use in treating diseases mediated by neurokinin-2 and/or neurokinin-3 (NK-3) receptors.
Solid-phase synthesis of 1,2,4-triazolidine-3,5-diones
Park, Kyung-Ho,Cox, Linda J
, p. 3899 - 3901 (2007/10/03)
A traceless synthesis of 1,2,4-triazolidine-3,5-diones has been achieved through cyclo-elimination from solid-phase. This traceless cyclo-elimination release step is induced by catalytic amount of base or by simply refluxing the urea carbamate intermediat
DICHLORONITROACETIC ACID DERIVATIVES AS ACYLATING AGENTS FOR PRIMARY AMINES, AMMONIA, AND PHENYLHYDRAZINE
Yurtanov, A. I.,Adkhamova, Z. M.,Baidildaeva, S. K.
, p. 891 - 894 (2007/10/02)
The corresponding carbamic acid derivatives were obtained (28-91percent) yields) as a result of the reaction of dichloronitroacetic acid derivatives, O2NCCl2COR, (1a-c, R=OEt, OCH2Ph, NH2) with ammonia, methylamine, benzylamine, glycine, phenylhydrazine, and aniline. The probable mechanism of the process and factors that affect the nature of the departing group were discussed. Keywords: dichloronitroacetic acid derivatives, aminolysis, intermediate states, mechanisms of reactions.
Synthesis of 3(S)-acylamino-1-[(phenyl)-(1H-tetrazol-5-yL)amino]-2-azetidinones
Atherton,Lambert
, p. 2599 - 2608 (2007/10/02)
1-Phenyl-1-(1-benzyl-1H-tetrazol-5-yl)hydrazine has been synthesized from N1-benzyloxycarbonyl-N2-phenylhydrazide and benzyl isothiocyanate. Coupling with N-(benzyloxycarbonyl)-L-serine 3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl ester
