65578-58-7Relevant academic research and scientific papers
A Modular Approach to Arylazo-1,2,3-triazole Photoswitches
Olson, David E.,Tombari, Robert J.,Tuck, Jeremy R.,Yardeny, Noah
supporting information, p. 4305 - 4310 (2021/06/28)
Azoheteroarenes make up an emerging class of photoswitchable compounds with unique photophysical properties and advantages over traditional azobenzenes. Therefore, methods for synthesizing azoheteroarenes are highly desirable. Here, we utilize azide-alkyne click chemistry to access arylazo-1,2,3-triazoles, a previously unexplored class of azoheteroarenes that exhibit high thermal stabilities and near-quantitative bidirectional photoconversion. Controlling the catalyst or 1,3-dipole grants access to both regioisomeric arylazotriazoles and arylazoisoxazoles, highlighting the versatility of our approach.
Preparation method of silver-mediated N-arylhydrazine compound
-
Paragraph 0044-0047, (2021/08/14)
The invention relates to a preparation method of an N-aryl hydrazide compound, which comprises the following steps: adding AgF, a reactant I, a reactant II, butanone and a magneton 5 into a reactor in sequence, connecting a condenser pipe, introducing condensate water from bottom to top, placing the reactor in an oil bath pan at 30-70 DEG C, heating, stirring and reacting for 10-12 hours, terminating the reaction, and purifying the product to obtain the N-aryl hydrazide compound. The method is mild in reaction condition, high in selectivity, relatively high in yield and environment-friendly; and the compound has certain biological activity and can be used in the field of synthesis of drugs, pesticides and paint dyes.
A search for blues brothers: X-ray crystallographic/spectroscopic characterization of the tetraarylbenzidine cation radical as a product of aging of solid magic blue
Talipov, Marat R.,Hossain, Mohammad M.,Boddeda, Anitha,Thakur, Khushabu,Rathore, Rajendra
supporting information, p. 2961 - 2968 (2016/03/12)
Magic blue (MB+? SbCl6- salt), i.e. tris-4-bromophenylamminium cation radical, is a routinely employed one-electron oxidant that slowly decomposes in the solid state upon storage to form so called 'blues brothers', which often complicate the quantitative analyses of the oxidation processes. Herein, we disclose the identity of the main 'blues brother' as the cation radical and dication of tetrakis-(4-bromophenyl)benzidine (TAB) by a combined DFT and experimental approach, including isolation of TAB+? SbCl6- and its X-ray crystallography characterization. The formation of TAB in aged magic blue samples occurs by a Scholl-type coupling of a pair of MB followed by a loss of molecular bromine. The recognition of this fact led us to the rational design and synthesis of tris(2-bromo-4-tert-butylphenyl)amine, referred to as 'blues cousin' (BC: Eox1 = 0.78 V vs. Fc/Fc+, λmax(BC+?) = 805 nm, εmax = 9930 cm-1 M-1), whose oxidative dimerization is significantly hampered by positioning the sterically demanding tert-butyl groups at the para-positions of the aryl rings. A ready two-step synthesis of BC from triphenylamine and the high stability of its cation radical (BC+?) promise that BC will serve as a ready replacement for MB and an oxidant of choice for mechanistic investigations of one-electron transfer processes in organic, inorganic, and organometallic transformations.
Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino- N -Boc-enamines
Tayama, Eiji,Kobayashi, Yoshiaki,Toma, Yuka
supporting information, p. 10570 - 10573 (2016/09/02)
Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines was demonstrated. The scope and limitation, experimental mechanistic studies, and a proposed reaction mechanism were also described.
Amination of Arylboronic Compounds via the Copper-Catalyzed Addition of Arylboronic Esters to Azodicarboxylates
Uemura, Takeshi,Yamaguchi, Mao,Chatani, Naoto
, p. 3746 - 3750 (2015/11/28)
Arylboronic esters add to di-tert-butyl azodicarboxylate under mild reaction conditions (at room temperature) to afford aryl-substituted hydrazine derivatives in good yields. The reaction tolerates a wide variety of functional groups.
Ene-hydrazide from enol triflate for the regioselective Fischer indole synthesis
Lim, Byeong-Yun,Jung, Bo-Eun,Cho, Cheon-Gyu
supporting information, p. 4492 - 4495 (2015/01/09)
Ene-hydrazide prepared from enol triflate undergoes a Fischer indolization reaction to give the corresponding indole with complete regioselectivity. The starting enol triflate is readily accessed in regiochemically defined form from the ketone precursor via various well-established methods. This new protocol was successfully applied to the synthesis of desbromoarborescidine A, a natural β-carboline alkaloid, difficult to prepare with conventional Fischer indole synthesis.
A mild and green method for the N-BOC protection of amines without assistant of catalyst under solvent-free conditions
Mojtahedi, Mohammad Majid,Niknejad, Nina,Veisi, Hojat
, p. 121 - 125 (2013/07/26)
A facile, green and versatile method for the Boc protection of amines has been developed by a treatment with (Boc)2O without any additive at room temperature. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines. The advantages of this method are green, simplicity, short reaction times and excellent yields.
An efficient Pd-catalyzed coupling of hydrazine derivatives with aryl halides
Ma, Fang-Fang,Peng, Zhi-Yong,Li, Wan-Fang,Xie, Xiao-Min,Zhang, Zhaoguo
supporting information; experimental part, p. 2555 - 2558 (2011/12/04)
A convenient method for the intermolecular N-arylation of hydrazides with aryl halides in the presence of a palladium catalyst, a MOP-type ligand, and Cs2CO3 is reported. The reaction gives coupling products in good to excellent yiel
Phenanthroline ligands in aryl palladium hydrazinato complexes: Catalysts for efficient coupling of azo componds with aryl boronic acids
Muniz, Kilian,Iglesias, Alvaro
, p. 6350 - 6353 (2008/04/05)
(Chemical Equation Presented) An easy couple: A new protocol for the synthesis of N-arylated amides, based on a coupling between azodicarboxylates and aryl boronic acids, has been developed (see scheme). Palladadiaziridines serve as catalysts for this pro
Copper salt catalyzed coupling of organobismuth reagents and azo compounds
T?ubrik, Olga,Kisseljova, Ksenija,M?eorg, Uno
, p. 2391 - 2394 (2008/02/09)
A new copper salt catalyzed C-N coupling is described. This smooth reaction between azo compounds and organobismuth reagents provides efficient and highly regioselective access to Boc-protected aryl hydrazines. The yields under optimized conditions are mo
