Summary
The one pot reaction of acetylacetone, CS2, and tetrabromobenzoquinone in a 2:2:1 molar ratio affords 2,6-di-(1-acetyl-2-oxopropylidene)-bidithiolo-(4,5-b:4′5′-e)-4,8-benzoquinone (3) which was allowed to react with some active methylene reagents in a 1:2 molar ratio to give the dispiro derivatives5–11. The reaction is assumed to proceedvia a hydrolysis of the two acetyl groups in compound3 followed by a nucleophilic addition of the active methylene reagents at the two ethylenic bonds and subsequent cyclization.
Zusammenfassung
Die Eintopfreaktion von Acetylaceton, CS2 und Tetrabrombenzochinon in einem molaren Verhältnis von 2:2:1 liefert 2,6-Di-(1-acetyl-2-oxopropyliden)-bidithiolo-(4,5-b:4′,5′-e)-4,8-benzochinon (3), das anschließend mit aktivierten Methylenverbindungen im Verhältnis 1:2 zu den Dispiroverbindungen5–11 umgesetzt wurde. Die Reaktion verläuft offenbar über eine Hydrolyse der beiden Acetylgruppen in Verbindung3, gefolgt von einer nucleophilen Addition der aktiven Methylengruppen an die ethylenischen Doppelbindungen und anschließender Cyclisierung.
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Soliman, A.M., Sultan, A.A. & El-Shafei, A.K. Synthesis of some new dispiro[dipyrano-(2,4′:6,4″)bidithiolo(4,5-b:4′,5′-e)-4,8-benzoquinones]. Monatsh Chem 126, 615–619 (1995). https://doi.org/10.1007/BF00807437
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DOI: https://doi.org/10.1007/BF00807437