ISSN:
0170-2041
Keywords:
Enamino ketones
;
Pictet-Spengler reactions
;
β-Carbolines, 1,2,3,4-tetrahydro-
;
Indoles, 2-substituted
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Reaction of tryptamine (1) with 2 and 3 gives the enamino ketones 4a and 5, resp., which on treatment with trifluoroacetic acid lead to the 2-substituted indoles 8 and 9, respectively. Acylation of 4a followed by reaction with trifluoroacetic acid or a Lewis acid affords the 1,2,3,4-tetrahydro-β-carbolines 7b-e in excellent yields. Treatment of 8 with anhydrides like (CF3CO)2O also yields the 1,2,3,4-tetrahydro-β-carboline 7f. The trichloromethylcarbonyl group in 7 can easily be converted into an ester moiety by reaction with an alcohol in the presence of K2CO3.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201175
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