ISSN:
0170-2041
Keywords:
Phenacylamines
;
Indoles
;
Indolo[2,1-b][3]benzazepines
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The intramolecular cyclization of N,N-disubstituted 2′-halogenophenacylamine hydrobromides 1a-h to 1,1-disubstituted 3-oxoindolinium bromides 3a-f has been studied. Some 3-oxoindolinium salts have also been prepared according to a different pattern by intramolecular cyclization of the phenacyl halides resulting from the bromination of 2′-(dialkylamino)acetophenones 4 or from the treatment of 2′-(dialkylamino)-2-diazoacetophenones 6a, b with hydrogen halides. Removal of hydrogen halide in salts 3a-g gives indolylio oxides 2a-g; these compounds have been shown to be unstable and decompose easily giving in general complex mixtures; only in the case of tetrahydroisoquinoline-derived ylides 2e, g we have observed clear-cut reactions leading, via a Stevens rearrangement followed by oxidation, to the 6,7-dihydro-13H-indolo[2,1-b][3]benzazepin-13-ones 8a, b.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940708
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