SYNTHESIS OF 1-AZAAZULENES USING RING-OPENING CYCLIZATION OF SPIROCYCLOPROPANE WITH AMINE

Synthesis of 1-azaazulenes using ring-opening cyclization of spirocyclopropane with a primary amine was accomplished. The reaction of cycloheptane-1,3-dione-2-spirocyclopropane with 2,4-dimethoxybenzylamine in refluxing acetonitrile resulted in a 94% yield of 1,2,3,6,7,8-hexahydrocyclohepta[b]pyrrol-4(5H)-one. The obtained product was successfully converted into 1-azaazulenes by deprotecting the amino-protecting group followed by oxidation.

Automated summary

The synthesis of 1-azaazulenes was achieved by ring-opening cyclization of spirocyclopropane with a primary amine. The obtained product was successfully converted into 1-azaazulenes after deprotecting the amino-protecting group followed by oxidation, yielding 94%.