Bis(sulfanediyl)bis(6-aminopyrimidin-4-ones): Versatile precursors for novel bis(sulfanediyl)bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones) linked to aliphatic spacer via multi-component reactions

Abstract

A synthesis of novel bis(sulfanediyl)bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones), linked to aryl, heteroaryl, and spirocyclic-oxindole moieties at position-5, as novel hybrid molecules was reported. 2,2'-(Butane-1,4-diylbis(sulfanediyl))bis(6-aminopyrimidin-4(1H)-one) was utilized as a precursor to our target compounds via a multicomponent reaction with two equivalents of both of the appropriate aldehyde and dimedone. The target compounds were alternatively obtained by bis-(alkylation) of the appropriate 5-aryl-2-thioxohexahydropyrimido[4,5-b]quinoline-4,6-dione with 1,4-dibromobutane in moderate basic medium.

Graphical Abstract

Keywords:

• Aliphatic spacer
• bis(6-aminopyrimidin-4-ones)
• bis(sulfanediyl)
• bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones)
• multi-component reactions