Synthesis and biological activity of dienediaminoketones of the indolin-3-one and 2-pyrrolin-4-one series

Design and Synthesis of Pyrano[3,2-b]indolones Showing Antimycobacterial Activity

“…In the next stage, the acetylation of indoles 5 at the 3-position with acetyl chloride led to acetates 6 . The treatment of 2-formyl-1 H -indoles ( 6 ) by malononitrile in the presence of triethylamine provided the major intermediates: 2-(2,2-dicyanovinyl)-1 H -indoles ( 7 ) . The key processcyclization and pyrano­[3,2- b ]­indolone formationwas conducted using concentrated hydrochloric acid in refluxing acetonitrile to yield target compounds 8 .…”

“…Synthesis of 4-(Methylthio)-2-oxo-2,5-dihydropyrano[3,2b]indole-3-carbonitrile (16). A mixture of 15 (0.01 mmol) and hydrogen chloride solution in dioxane (0.02 mmol) in methanol was refluxed for 2 h. The cooled reaction mixture was filtered, and the precipitate was recrystallized from a DMF−methanol mixture.…”

“…The treatment of 2-formyl-1H-indoles (6) by malononitrile in the presence of triethylamine provided the major intermediates: 2-(2,2-dicyanovinyl)-1H-indoles (7). 16 The key process cyclization and pyrano[3,2-b]indolone formationwas conducted using concentrated hydrochloric acid in refluxing acetonitrile to yield target compounds 8. 12 In Vitro Antimicrobial Activity and Cytotoxicity Studies of Novel Pyrano [3,2-b]indolones.…”

C-Vinylpyrroles as Pyrrole Building Blocks

“…Pyrrolone 207 may be prepared directly from the vinylpyrrole 205 by heating in a 2-propanol solution with piperidine for 2 h (Scheme 74). 65 Acidification of salt 206 gives 2-methyl-3-ethoxycarbonyl-4-hydroxy-5-(2,2-dicyanovinyl)pyrrole (208). Treatment of the latter with amines readily affords pyrrolones 209.…”

“…Brief reflux of 2-vinylpyrrole 205 in 2-propanol with piperidine results in salt 206 , which transforms to pyrrolone 207 on longer reflux. Pyrrolone 207 may be prepared directly from the vinylpyrrole 205 by heating in a 2-propanol solution with piperidine for 2 h (Scheme ) 74 …”