Synthesis of 1-substituted 2-azaspiro[4.5]deca-6,9-diene-8-ones and 2-azaspiro[4.5]deca-1,6,9-triene-8-ones by a three-component condensation of 1,2,3-, 1,2,4- or 1,3,5-trimethoxybenzene with isobutyric aldehyde and nitriles

A three-component condensation of 1,2,3- or 1,2,4-trimethoxybenzene with isobutyric aldehyde and alkyl cyanoacetates in the presence of sulfuric acid resulted in the formation of substituted 2-azaspiro[4.5]deca-6,9-diene-8-ones. The same reaction of aromatic nitriles yielded 2-azaspiro[4.5]deca-1,6,9-triene-8-ones; in the case of 1,2,3-trimethoxybenzene corresponding Ritter amides were also observed. The condensation of 1,3,5-trimethoxybenzene with isobutyric aldehyde and alkyl cyanoacetates provided the compounds of the formal Knöevenagel condensation.

Figure optionsDownload as PowerPoint slide