37914-61-7Relevant academic research and scientific papers
C-2 SIDE CHAIN ALKYLATION OF 2-METHYL-3-ALKYLINDOLES VIA 3-METHOXYINDOLENINES
Vice, Susan F.,Gross, Edward A.,Friesen, Richard W.,Dmitrienko, Gary I.
, p. 829 - 832 (2007/10/02)
3-Methoxyindolenines derived from 2-methyl-3-alkylindoles by bromination-methanolysis undergo base induced alkylation and aldol condensations at the C-2 methyl group.The modified indolenines can be efficiently converted to C-2-side chain alkylated indoles
The bromination-methanolysis of N-acetyl-2,3-dimethylindole
Vice, Susan F.,Dmitrienko, Gary I.
, p. 1233 - 1237 (2007/10/02)
Bromination of N-acetyl-2,3-dimethylindole 11 in the presence of excess methanol at room temperature gave a mixture of products consisting of cis and trans N-acetyl-2,3-dimethoxy-2,3-dimethylindoline 17 and 18, 3-methoxy-2,3-dimethylindoline 19, and N-acetyl-3-methoxymethyl-2-methylindole 21.The same reaction performed at -40 degC yielded a mixture of 17, 18, and N-acetyl-2-methoxy-2-methyl-3-methyleneindoline 22.Bromination of 11 at low temperature in the presence of 1.5 equivalents of methanol followed by treatment with triethylamine yielded 22 quantitatively.Treatment of 22 with acidic methanol readily gave 21.The mechanistic implications of these transformations are considered.
The bromination and chlorination of 2,3-dialkylindoles. Isolation of 3-bromo- and 3-chloro-2,3-dialkylindolenines and acid catalyzed conversion to 3-methoxyindolenines
Dmitrienko, Gary I.,Gross, Edward A.,Vice, Susan F.
, p. 808 - 814 (2007/10/02)
The bromination of 2,3-dimethylindole in acetic acid followed by hydrolysis has been shown to yield the known dimer 16 of 3-hydroxy-2,3-dimethylindolenine 15 and not 3-hydroxymethyl-2-methylindole 12 as reported previously by others.Bromination of 2,3-dimethylindole in the presence of triethylamine has yielded 3-bromo-2,3-dimethylindolenine 17 as a crystalline solid which is stable at room temperature in a nitrogen atmosphere in the presence of triethylamine but decomposes vigorously in the absence of base.Under mildly acidic conditions 17 reacts rapidly with methanol to yield 3-methoxy-2,3-dimethylindolenine 3 in good yield.With tert-butyl hypochlorite in the presence of triethylamine, 2,3-dimethylindole gives 3-chloro-2,3-dimethylindolenine 2 which has chemical properties similar to 17 reacting readily with methanol to give 3.Similarly tetrahydrocarbazole was converted to the analogous chloroindolenine 5 and bromoindolenine 18 both of which readily underwent methanolysis to give 6 in good yield.A mechanism for the acid catalyzed methanolysis of 3-chloro- and 3-bromoindolenines is proposed.
Alkoxylation of 2,3-dialkylindoles utilizing iodosobenzene diacetate
Awang, Dennis V. C.,Vincent, Andre
, p. 1589 - 1591 (2007/10/02)
Iodosobenzene diacetate has been employed in the development of a simple procedure for the production of 3-alkoxyindolenines from 2,3-disubstituted indoles, by treatment of the indoles with the reagent in alcoholic solvent.Primary and secondary alkoxy fun
