53676-44-1Relevant academic research and scientific papers
A SIMPLE ROUTE TO INDOLE-2,3-QUINODIMETHANE-A FACILE SYNTHESIS OF CARBAZOLES
Saroja, B.,Srinivasan, P. C.
, p. 5429 - 5430 (1984)
2,3-Dimethylindole is easily converted into N-benzoyl-2,3-dibromo methylindole, the latter upon treatment with sodium iodide in DMF in the presence of a suitable dienophile furnishes a carbazole derivative.
Fluorine as a Traceless Directing Group for the Regiodivergent Synthesis of Indoles and Tryptophans
Andries-Ulmer, Anna,Brunner, Christoph,Rehbein, Julia,Gulder, Tanja
supporting information, p. 13034 - 13041 (2018/09/27)
Despite ample evidence for the unique reactivity offered by hypervalent F-iodanes, mechanistic investigations fall far behind. In order to shed light on the unusual behavior of such F-reagents, we conducted computational and experimental studies on the chemodivergent transformation of styrenes. We identified the spirocyclic F-cyclopropane as the common intermediate for both the C,H-fluorination and C,H-amination pathways. The fate of this key compound is determined by the extent of cationic charge delocalization controlled by the N-substituents. Exploiting this phenomenon, a multitude of different transformations have become available, leading, i.e., to the regiodivergent synthesis of indoles and tryptophans.
A new approach to 3-substituted tetrahydro-β-carboline derivative via diethyl acetamidomalonate
Kotha, Sambasivarao,Misra, Shilpi,Mobin, Shaikh M.
, p. 933 - 936 (2012/03/22)
Strategically a new approach for the synthesis tetrahydro-β-carboline unit with the aid of diethyl acetamidomalonate as a glycine equivalent has been described. Springer-Verlag 2010.
Role of 2-naphthyl ether intermediate in formation of isolable atropisomers derived from the coupling reaction of (2-hydroxy-3,3-dimethylindolin-l-yl)-(substituted phenyl)methanones with 2-naphthol
Eto, Masashi,Ito, Fumikazu,Sato, Hidetoshi,Shinohara, Itaru,Yamaguchi, Koki,Yoshitake, Yasuyuki,Harano, Kazunobu
experimental part, p. 1485 - 1496 (2009/12/24)
The formation pathway of the atropisomers derived from the reaction of (2-hydroxy-3,3-dimethylindolin-l-yl)(4-substituted phenyl)methanones with 2-naphthol in the presence of BF3·Et2O was discussed on the basis of the isolation of the 2-naphthyl ether intermediate whose structure was determined by single crystal X-ray analysis. The results indicate that the coupling reaction proceeds through stepwise mechanism, i.e., the ether intermediate formation followed by Fries-type rearrangement.
Acylation, cyanoethylation and alkylation of methyl and phenyl indolylmagnesium salts: Influence of the substituents on the C- and N- reaction products
Rodriguez, J. Gonzalo,Urrutia, Anahi
, p. 129 - 135 (2007/10/03)
Analysis of the influence of the substitution on indolylmagnesium salts in the reaction with benzoyl chloride, acrylonitrile and methyl iodide, giving the C- and N-derivatives, have been carried out. The yield in the C- and N-product depends upon the electronic character and position of the substituent (methyl or phenyl) on the indole ring and of the ethereal solvent as well as the concentration and molar ratio of the reagents. The 2- or 3- phenyl substituted indolylmagnesium salts with acrylonitrile always gave the 1-(2-cyanoethyl)indole derivative.
