Publication detail

Unusual ring transformation of 5-(2-aminophenyl)-2-aryl-1,3-thiazol-4(5H)-ones to 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones

Authors: Hanusek Jiří | Kammel Richard | Tarabová Denisa

Year: 2016

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	Unusual ring transformation of 5-(2-aminophenyl)-2-aryl-1,3-thiazol-4(5H)-ones to 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones	Recently we have described unexpected reaction of 3-bromo-1,3-dihydro-2H-indol-2-one (1) with 4-methoxythiobenzamide giving product of Eschenmoser coupling reaction i.e. (3Z)-3-[amino(4-methoxyphenyl)-methylidene]-1,3-dihydro-2H-indol-2-one (2a). However when we tried to extend this synthetic protocol to other aromatic thioamides we have found that the structure of intermediate formed in acetonitrile corresponds to 5-(2-aminophenyl)-2-aryl-1,3-thiazol-4(5H)-ones (3a-h) which subsequently rearranges to Eschenmoser coupling product (2a-h). Therefore our communication will concern targeted synthesis and characterization of both heterocyclic systems, conditions necessary for transformation of 3a-h to 2a-h and mechanism of this transformation. Fluorescence properties of 5-(2-aminophenyl)-2-aryl-1,3-thiazol-4(5H)-ones (3a-h) will be also discussed in the context with our recent paper dealing with structurally similar 5-(2-hydroxyphenyl)-2-aryl-1,3-thiazol-4(5H)-ones.

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