Synthesis and antimicrobial activity of 2-aroylmethylene-6-hydroxy-2,3-dihydroindol-3-ones

Abstract

The interaction of methyl esters of aroylpyruvic acids with 2-aminophenol was used to form 2-aroylmethylene-6-hydroxy-2,3-dihydroindol-3-ones. The structures of these compounds were verified by IR and 1 H NMR spectroscopy; the antimicrobial activity of the compounds synthesized here was studied.

Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones

“…The reaction in polar aprotic solvents, such as DMSO and DMF, was also tested. It was found that the outcome of these reactions also improves in the presence of water, but the overall performance in these solvents remains relatively poor (entries [10][11][12][13].…”

“…1). [10][11][12][13][14][15][16][17] Normally, preparation of such compounds relies heavily on the chemistry of isatins, which makes synthetic approaches to certain substitution patterns hardly accessible. An alternative synthetic platform for assembling indoline alkaloids and related non-natural, biologically active target molecules has also emerged, relying on the chemistry of 2alkylidene-3-oxindoles.…”

“…An alternative synthetic platform for assembling indoline alkaloids and related non-natural, biologically active target molecules has also emerged, relying on the chemistry of 2alkylidene-3-oxindoles. [18][19][20][21][22][23] Various synthetic approaches to these synthons have been developed based on the aldol condensation of 3H-indol-3-ones with carbonyl compounds (path A, Scheme 1), [24][25][26][27][28] transition metal-catalyzed carbonylative coupling of ortho-iodoanilines to acetylenes (path B, Scheme 1), [29][30][31][32] and cascade reactions of anilines with a-ketoesters involving an electrophilic aromatic substitution step (path C, Scheme 1) 10,33 Herein we wish to report on our recent serendipitous discovery of the unexpected one-pot cascade transformation of ortho-nitrochalcones 1 via a Baeyer-Drewson-like pathway, but affording 2-alkylideneindolin-3-ones 2 rather than indigo-like dimers (Scheme 1).…”

Oxidative Cyclization of 4-(2-Aminophenyl)-4-oxo-2-phenylbutanenitriles into 2-(3-Oxoindolin-2-ylidene)acetonitriles

“… 2 − 7 2-Alkylideneindolin-3-one derivatives bearing a single indoline moiety or two remotely positioned indoline subunits are found in nature and are endowed with important biological activities as well. 8 − 15 2-Alkylideneindolin-3-ones bearing a conjugated nitrile function (i.e., 2-(3-oxoindolin-2-ylidene)acetonitriles 1 ) were used as advanced precursors in the synthesis of pyridazino[4,3- b ]indoles 2 , which possess strong inhibitory activity against Mycobacterium tuberculosis ( Scheme 1 ). 16 Recently, we have communicated on the unexpected formation of 2-alkylideneindolin-3-ones taking place upon treatment of ortho -nitrochalcones with potassium cyanide and acetic acid in methanol.…”

2-Iodoisatogens: Versatile Intermediates for the Synthesis of Nitrogen Heterocycles

“…These compounds are relatively rare and have been far less studied with respect to their biological activity or cycloaddition chemistry as compared to the 2-oxindole isomers. Moreover, current methods for generating these compounds are rather limited and generally low yielding . We therefore investigated a two-step displacement-decarboxylation sequence toward these products, and our results are summarized in Scheme .…”