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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 |
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| Authors: | Vladimir A Glushkov Olga G Stryapunina Olga A Maiorova Sandra Ya Ryabukhina Valentina I Sokol |
| Institution: | a Institute of Technical Chemistry, Urals Branch of the Russian Academy of Sciences, Academician Korolev Street 3, Perm 614013, Russia b I. Ya. Postovsky Institute of Organic Synthesis, Urals Branch of the Russian Academy of Sciences, S. Kovalevskoy Street 22, Ekaterinburg 620041, Russia c Perm State University, Bukireva Street 15, Perm 614990, Russia |
| Abstract: | 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-azaspiro4.5]deca-6,9-diene-8-ones. The same reaction of aromatic nitriles yielded 2-azaspiro4.5]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. |
| Keywords: | 1 3 5-Trimethoxybenzene Nitriles 2-Azaspiro[4 5]deca-6 9-diene-8-ones Three-component condensation |
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