In:
Canadian Journal of Chemistry, Canadian Science Publishing, Vol. 58, No. 8 ( 1980-04-15), p. 808-814
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
0008-4042
,
1480-3291
Language:
English
Publisher:
Canadian Science Publishing
Publication Date:
1980
detail.hit.zdb_id:
1482256-8
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