697-86-9Relevant articles and documents
Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals
Shen, Tao,Zhu, Bencong,Lin, Fengguirong,Pan, Jun,Wei, Jialiang,Luo, Xiao,Liu, Jianzhong,Jiao, Ning
supporting information, p. 815 - 818 (2018/07/31)
A direct and structurally divergent synthesis of indole alkaloids from very simple 2-vinylanilines, alkynes and TBN via a novel substrate fragmentation/cycloaddition strategy has been developed, which provides an efficient noble-metal-free approach to access a library of highly valuable indole derivatives of tryptamines and tryptamine-related oximes, lactams, and lactones, as well as β-carbolines, spiroindolines, and hexa-hydropyrrolo[2,3-b]indoles.
Lewis acid-promoted synthesis of unsymmetrical and highly functionalized carbazoles and dibenzofurans from biaryl triazenes: Application for the total synthesis of clausine C, clausine R, and clauraila A
Yang, Weijun,Zhou, Jun,Wang, Binjie,Ren, Hongjun
supporting information; scheme or table, p. 13665 - 13669 (2012/01/15)
A natural approach: A Lewis acid-promoted nucleophilic aromatic substitution approach to the regioselective synthesis of highly substituted carbazoles and dibenzofurans has been developed. The annulation process is applied to the total synthesis of carbazole alkaloids clausine C, clausine R, and clauraila A (see scheme).
Identification of bromination products of chloro-substituted anilines in aqueous environment by gas chromatography
Gruzdev,Filippova,Zenkevich,Kondratenok
experimental part, p. 1748 - 1759 (2012/02/15)
To reduce the detection limits of aniline and its various chloroderivatives (all isomers of mono- and dichloroanilines, 2,4,5 -, 2,4,6-, and 3,4,5-trichloroanilines, pentachloroaniline) in aqueous media we suggested bromination reaction, followed by gas chromatographic definition bromo derivatives of chloroanilines on a selective electron capture detector. To identify the products of bromination of chloroaniline in combination with mass-spectrometric data we used chromatographic retention indices on standard nonpolar polydimethylsiloxane stationary phase that was determined for 50 compounds in this class. The technique of identifying bromoderivatives of chloroaniline in water was developed at the gas-chromatographic analysis in the selective electron capture detector. To improve the reliability of the identification of additional bromoderivatives of chloroanilines we obtained their trifluoroacetyl derivatives.
The electrophilic substitution of some 2,4- and 2,6- dihaloacetanilides
Hanson, James R.,Saberi, Hamid
, p. 699 - 701 (2007/10/03)
The orientation of electrophilic substitution of some 2,4- and 2,6-dihaloacetanilides has been examined by NMR methods. Mixed acid nitration of 2,6-dichloro and 2-chloro-6-methylacetanilides gave predominantly the 3-nitro derivatives.
Solid state nuclear bromination with N-bromosuccinimide. Part 1. Experimental and theoretical studies on some substituted aniline, phenol and nitro aromatic compounds
Sarma, Jagarlapudi A.R.P.,Nagaraju, Akula
, p. 1113 - 1118 (2007/10/03)
Solid state bromination of a number of substituted phenol, aniline and nitro aromatic compounds with N-bromosuccinimide yields exclusively the nuclear brominated products. Reactivity in the solid state depends on the reaction time, temperature and nature of the substituent on the substrate. The reaction apparently proceeds by an electrophilic aromatic substitution pathway. Molecular orbital and reaction free energy calculations also support such a view. Thermal analysis and video microscopic observation reveal the nature of the solid state reaction. Crystallinity is required for the reactivity and product selectivity. Product yield decreases with loss of selectivity when the reaction is carried out in a melt or in solution. Unlike the topochemical solid state reactions wherein molecular packing is more important than the intrinsic reactivity, these reactions demonstrate the importance of both these factors.
Efficient Catalysis of Hydrodediazoniations in Dimethylformamide
Wassmundt, Frederick W.,Kiesman, William F.
, p. 1713 - 1719 (2007/10/02)
For hydrodediazoniations (the replacement of a diazo group by hydrogen) in DMF, several substances act as catalysts through their ability to serve as electron donors and initiate free-radical reactions.A general procedure has been developed in which FeSO4 speeds the conversion and leads to higher yields.Trapping experiments demonstrated the presence of free-radical intermediates.N,N-Dimethylacetamide was found to rival DMF as a source of hydrogen atoms.
