1089-82-3Relevant academic research and scientific papers
Deoxygenation Reactions of ortho-Nitrostyrenes with Carbon Monoxide Catalysed by Metal Carbonyls: a New Route to Indoles
Crotti, Corrado,Cenini, Sergio,Rindone, Bruno,Tollari, Stefano,Demartin, Francesco
, p. 784 - 786 (1986)
The metal carbonyls Fe(CO)5, Ru3(CO)12, and Rh6(CO)16 are catalysts for the deoxygenation of ortho-nitrostyrenes under carbon monoxide pressure to give indole derivatives; the crystal structure of a non-catalytically active rhodium complex obtained during the synthesis of (5e) is reported.
Nitrenium ions. ? reactions of N,N-dimethyl-p-benzoyloxyaniline-iminium chloride with indoles and indolizines. X-ray structure of unexpected [2-chloro-4-(4-dimethylaminophenyl-ONN-azoxy)-phenyl]dimethylamine (azoxy derivative)
Greci, Lucedio,Castagna, Riccardo,Carloni, Patricia,Stipa, Pierluigi,Rizzoli, Corrado,Righi, Lara,Sgarabotto, Paolo
, p. 3768 - 3771 (2007/10/03)
N,N-Dimethyl-p-nitrosoaniline reacts with benzoyl chloride affording a complex salt containing a cation, a hybrid between a nitrenium ion and an iminium ion. The salt reacts with nucleophiles (indoles, indolizines) yielding compounds characterized by a new carbon-nitrogen bond, derived from the nitrenium ion form. According to the type of nucleophile, the reaction, to differing extents, is in competition with an electron transfer process which leads to the formation of the dimer of the nucleophile and of the azoxy corresponding to the N,N-dimethyl-p-nitrosoaniline. In one of the reactions studied, a chlorinated azoxy derivative was also isolated, and its structure was elucidated by X-ray analysis.
Nitrenium Ions. Part 1. Acid-catalysed Reactions of 2-Methylindole with Nitrosobenzenes. Crystal Structures of 2-Phenylamino-3-phenylimino-3H-indole, 2-(o-Tolylamino)-3-(o-tolylimino)-3H-indole, N-Phenyl-N-(2-phenylamino-3H-indol-3-ylidene)amine N-Oxide and Bis(2-methyl-1H-indol-3-yl)...
Cardellini, Liberato,Carloni, Patricia,Damiani, Elisabetta,Greci, Lucedio,Stipa, Pierluigi,et al.
, p. 1589 - 1596 (2007/10/02)
2-Methylindole 3b reacts with nitrosobenzenes 1a-c in the presence of monochloroacetic acid affording compounds which are characterized by the formation of carbon-nitrogen bonds and other compounds which clearly could arise from a radical mechanism.The radical component of the reaction is also supported by the EPR spectroscopy as well as the reaction products distribution.Although these reactions cannot be considered of synthetic value for the number of isolated products, they could be regarded as clear examples of the electrophilic character and of the oxidative power of nitrogen in activated nitrosobenzenes.Crystal structures of 2-phenylamino-3-phenylimino-3H-indole 7a, 2-(o-tolylamino)-3-(o-tolylimino)-3H-indole 7b, N-phenyl-N-(2-phenylamino-3H-indol-3-ylidene)amine N-oxide 9a and bis(2-methyl-1H-indol-3-yl)methane 10 are also reported.
The chlorination of indoles by copper(II) chloride
Balogh-Hergovich, Eva,Speier, Gabor
, p. 2305 - 2309 (2007/10/02)
The reaction of indoles with copper(II) chloride has been studied in acetonitrile.At low copper(II):indole ratios, dimers are formed in the presence of dioxygen, oxygenated products are obtained, and at large copper(II):indole ratios, pyrrole ring-chlorinated products are formed in yields of up to 92percent.The reactions are postulated to proceed via the radical cations of the indoles formed in an electron-transfer reaction.
