7164-92-3Relevant academic research and scientific papers
Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin
Yan, Jianwei,Ni, Tianjun,Yan, Fulin
supporting information, p. 1096 - 1098 (2015/02/19)
Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions.
Efficient synthesis of 3-selanyl- and 3-sulfanylindoles employing trichloroisocyanuric acid and dichalcogenides
Silveira, Claudio C.,Wolf, Lucas,Martins, Guilherme M.,Von Muehlen, Lisandro,Mendes, Samuel R.
, p. 10464 - 10469,6 (2012/12/12)
3-Arylselanyl- and 3-arylsulfanylindoles were prepared in EtOAc, by the reaction of indole with the diaryl dichalcogenide-trichloroisocyanuric acid (TCCA) reagent system. The products were efficiently and conveniently obtained, at room temperature and in
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.
Chlorination of 2-Methyl- and 2-Phenylindole with NaOCl. Formation of Intermediates and Their Reactions with Alkaline Methanol
Rosa, Michael De,Carbognani, Lante,Febres, Ayheza
, p. 2054 - 2059 (2007/10/02)
Chlorination of 2-methylindole (1) in carbon tetrachloride with excess sodium hypochlorite gave a 2:1 mixture of N,3-dichloro-2-methylindole (4) and 3,3-dichloro-2-methyl-3H-indole (5) in a total yield of 76-92percent.N-Chloro-2-methylindole (2) was detected when the chlorination was carried out with an indole to NaOCl ratio of 10:1.Sodium hypochlorite was found to promote the rearrangement of N-chloroindoles 2 and 4.The chlorination of 2-phenylindole (6) gave a mixture of N,3-dichloro-2-phenylindole (8) and 3,3-dichloro-2-phenyl-3H-indole (9) in a total yield of 81-92percent.The rearrangement of 8 to 9 was detected by IR and UV.This occurred in the presence or absence of NaOCl.Reactions of the dichloro intermediates with alkaline methanol gave a number of products.It is proposed that the N,3-dichloroindoles rearranged to their respective 3H-indoles in alkaline methanol and the products were formed by nucleophilic attack on either carbon (C-3) or chlorine of the 3H-indole.
