Publikace detail

Study of rearrangement of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones to 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles.

Autoři: Hanusek Jiří | Kammel Richard | Hladíková Veronika | Marek Lukáš

Rok: 2017

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

Tituly:

Jazyk	Název	Abstrakt	Klíčová slova
eng	Study of rearrangement of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones to 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles.	Recently we have observed unexpected behavior during the reaction of 3-bromo-1,3-dihydro-2H-indol-2-one (3-bromo-oxindole, 1a) with 4-methoxythiobenzamide giving a product arising from a Eschenmoser coupling reaction i.e. (3Z)-3-[amino(4-methoxyphenyl)-methylidene]-1,3-dihydro-2H-indol-2-one instead of the expected transformation product 5-(2-aminophenyl)-4-hydroxy-2-(4-methoxyphenyl)-1,3-thiazole. Deeper exploration4 of this reaction involving various substituted thiobenzamides has shown that the expected thiazole is formed first (kinetic control) but it is unstable and under thermodynamic control conditions rearranges to Eschenmoser coupling product (Scheme for R2 = H). In this work the influence of further substitution (R2) in starting 3-bromo-oxindole will be discussed due to potential application of this synthetic protocol for the preparation of highly effective kinase inhibitors1 (2H-indol-2-ones) and and/or fluorescent materials (thiazoles).

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