Kammel, Richard; Tarabova, Denisa; Broz, Bretislav; Hladikova, Veronika; Hanusek, Jiri published the artcile< Formation of 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones involving ring transformation of 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles>, Product Details of C9H9NO4, the main research area is Hammett correlation kinetics ring transformation aryl aminophenyl hydroxythiazole; amino arylmethylidene indolone preparation Eschenmoser coupling; ring transformation aryl aminophenyl hydroxythiazole kinetics.
The reaction of 3-bromooxindole with substituted (hetero)aromatic thioamides in acetonitrile was studied. At room temperature the reaction preferably gives products of ring transformation i.e. 2-aryl-5-(2-aminophenyl)-4-hydroxy-1,3-thiazoles whereas at elevated temperature products of an Eschenmoser coupling reaction, i.e. 3-[amino(aryl)-methylidene]-1,3-dihydro-2H-indol-2-ones, are formed exclusively. There exist only two exceptions (4-methoxy and 2-pyridinthioamide) in which the Eschenmoser coupling reaction always takes place. Also N-methylation of the starting 3-bromooxindole completely prevents formation of thiazoles. The prepared thiazoles are unstable in solution and they undergo slow ring transformation to the expected Eschenmoser coupling products. The rate limiting step of this rearrangement involves cleavage of an intermediary thiirane ring, which is slowed down by electron-withdrawing substituents on the thioamide (ρ = -1.15).
Tetrahedron published new progress about C-S bond (cleavage). 30095-98-8 belongs to class esters-buliding-blocks, and the molecular formula is C9H9NO4, Product Details of C9H9NO4.
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Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics