158092-56-9Relevant academic research and scientific papers
Synthesis of Quaternary Indoxyl Derivatives by Intramolecular Cyclization of Some Substituted Acetophenones
Ruiz, Jose R.,Aran, Vicente J.,Asensio, Juan L.,Flores, Maria,Stud, Manfred
, p. 679 - 684 (2007/10/02)
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-indolobenzazepin-13-ones 8a, b. - Key Words: Phenacylamines / Indoles / Indolobenzazepines
