35527-28-7Relevant academic research and scientific papers
Selective and Scalable Electrosynthesis of 2H-2-(Aryl)-benzo[d]-1,2,3-triazoles and Their N-Oxides by Using Leaded Bronze Cathodes
Wirtanen, Tom,Rodrigo, Eduardo,Waldvogel, Siegfried R.
supporting information, p. 5592 - 5597 (2020/04/15)
Electrosynthesis of 2H-2-(aryl)benzo[d]-1,2,3-triazoles and their N-oxides from 2-nitroazobenzene derivatives is reported. The electrolysis is conducted in a very simple undivided cell under constant current conditions with a leaded bronze cathode and a g
A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV = O Redox Cycling
Nykaza, Trevor V.,Harrison, Tyler S.,Ghosh, Avipsa,Putnik, Rachel A.,Radosevich, Alexander T.
, p. 6839 - 6842 (2017/05/29)
A small-ring phosphacycle, 1,2,2,3,4,4-hexamethylphosphetane, is found to catalyze deoxygenative N-N bond-forming Cadogan heterocyclization of o-nitrobenzaldimines, o-nitroazobenzenes, and related substrates in the presence of hydrosilane terminal reductant. The reaction provides a chemoselective catalytic synthesis of 2H-indazoles, 2H-benzotriazoles, and related fused heterocyclic systems with good functional group compatibility. On the basis of both stoichiometric and catalytic mechanistic experiments, the reaction is proposed to proceed via catalytic PIII/PV = O cycling, where DFT modeling suggests a turnover-limiting (3+1) cheletropic addition between the phosphetane catalyst and nitroarene substrate. Strain/distortion analysis of the (3+1) transition structure highlights the controlling role of frontier orbital effects underpinning the catalytic performance of the phosphetane.
Tert-butyl nitrite mediated regiospecific nitration of (E)-azoarenes through palladium-catalyzed directed C - H activation
Majhi, Biju,Kundu, Debasish,Ahammed, Sabir,Ranu, Brindaban C.
supporting information, p. 9862 - 9866 (2014/08/18)
An efficient protocol for the Pd-catalyzed regiospecific ortho-nitration of (E)-azoarenes has been achieved for the first time using tBuONO as a nitrating agent under atmospheric oxygen. A series of both symmetrical and unsymmetrical azoarenes were nitrated efficiently by this procedure providing excellent chemo- and regioselectivity and compatibility with a broad array of functional groups.
Synthesis of Azobenzenes from Quinone Acetals and Arylhydrazines
Carreno, M. Carmen,Mudarra, Gerardo Fernandez,Merino, Estibaliz,Ribagorda, Maria
, p. 3413 - 3416 (2007/10/03)
Direct reaction between quinone bisacetals and arylhydrazines gives azobenzenes. The presence of catalytic amounts of cerium ammonium nitrate strongly accelerates the reaction. When the bisacetal has a substituent at the 2,5-cyclohexadiene framework, only one regioisomer is formed. The method represents a simple, mild, and novel synthetic access to differently substituted azocompounds in high to excellent yield.
Preparation of Some 2-(Methoxyphenyl)-2H-benzotriazoles and the Corresponding Hydroxyphenyl Compounds
Rosevear, Judi,Wilshire, John F. K.
, p. 1663 - 1673 (2007/10/02)
The reaction of several substituted o-nitronitrosobenzenes with o- and p-anisidine, and 2,4-dimethoxyaniline in acetic acid gives in good yield the corresponding o-nitroazobenzenes which are readily reduced with thiourea dioxide (formamidinesulfinic acid) to the corresponding 2-(methoxyphenyl)-2H-benzotriazoles, demethylation of which furnished the corresponding 2-(hydroxyphenyl)-2H-benzotriazoles.Demethylation of the dimethoxy derivatives was best accomplished with boron tribromide in methylene chloride, the methoxy group located ortho to the benzotriazole ring beingdemethylated more readily than is the para-methoxy group.The reaction of 0-nitroazobenzenes containing a methoxy group with hydrobromic acid in acetic acid results in cleavage of the azo bond and also partial bromination to give o-nitroaniline and some of its brominated derivatives.
BASIC PROPERTIES OF 4-ARYLAZO-PHENOLS AND 4-ARYLAZO-ANISOLES
Nesterowicz, Marianna,Korewa, Ryszard
, p. 1085 - 1092 (2007/10/02)
The conditions in which 4-arylazo-phenols and 4-arylazo-anisoles have basic properties have been studied.We have also determined the equilibrium constants of the reactions between 4-arylazo-phenols or 4-arylazo-anisoles with perchloric acid in nitromethane, acetonitrile and acetic acid.Conclusions have been drawn from the influence of the nature of solvent and substituent at the benzene ring on equilibrium constant values.
