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Synthesis and antimicrobial activity of Bis-Derivatives of 3a′, 6a′Dihydro-2'H-Spiro[Indole-3,1'-Pyrrolo[3,4-c]Pyrrole]-2,4',6'(1H, 3'H, 5'H)-Trione

Ruslan Gryhorovych Redkin, Evgeniya Igorevna Syumka, Leonid Antonovich Shemchuk, Valentin Petrovych Chernykh.


The interaction of isatins, α-amino acids and 1,6-bismaleimidohexane has been studied. It was found that for 1'-R3-2'-R2-3'-R1-5'-(6-{1'-R3-2'-R2-3'-R1-2,4',6'-trioxo-1,2,3',3'a,4',5',6',6'a-octahydro-2'H-spiro[indole-3,1'-pyrrolo[3,4-c]pyrrole]-5'-yl}hexyl)-1,2,3',3'a,4',5',6',6'a-octahydro-2'H-spiro[indole-3,1'-pyrrolo[3,4-c] pyrrole]-2,4',6'-triones were formed through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the decarboxylative condensation of isatin and α-amino acid with dipolarophile 1,6-bismaleimidohexane. This method has the advantages of mild reaction conditions, high atom economy and excellent yields. The most suitable conditions for this reaction are boiling alcohol-water medium. The obtained compounds showed a weak selective antimicrobial activity for the Micrococcaceae family.

Key words: isatins, α-amino acids, 2-oxindoles; bis-spirocyclic systems; bis-maleimides, 1,3-cycloaddition, antimicrobial activity

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