Synthesis of Novel Bis(Sulfanediyl)Bis(Tetrahydropyrimido[4,5-b]Quinoline-4,6-Diones) Linked to Butenyl and Butynyl Spacers via Thioether Linkages

Abstract

A synthesis of novel bis(tetrahydropyrimido[4,5-b]quinoline-4,6-diones) connected to butenyl and butynyl spacers via thioether linkages is reported. Two equivalents of the appropriate aldehyde and dimedone were used in a multicomponent reaction with the corresponding bis(6-aminopyrimidin-4(3H)-ones) to produce the target products. Bis(alkylation) of the appropriate 2-thioxohexahydropyrimido[4,5-b]quinoline-4,6-dione in ethanolic potassium hydroxide with 1,4-dichlorobut-2-ene or 1,4-dibromobut-2-yne also produced the target compounds. Furthermore, bis(tetrahydropyrimido[4,5-b]quinolinetriones) linked to olefinic or acetylenic spacers via ether linkage were synthesized in high yields by a three-component reaction of the appropriate bis(aldehydes) with two equivalents of both 6-aminothiouracil and dimedone.