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Synthesis of 2-(1,4-dioxaspiro[4.5]decan-6-yl)acrylamides from 2-acetylcyclohexanone via palladium-catalysed aminocarbonylation

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Abstract

6-(1-Iodovinyl)-1,4-dioxaspiro[4.5]decane, an iodoalkene obtained from 2-acetylcyclohexanone via ethylene ketal formation, hydrazone formation and iodination, was aminocarbonylated in the presence of a palladium-phosphine precatalyst. Systematic investigations revealed that 2-(1,4-dioxaspiro[4.5]decan-6-yl)acrylamides can be obtained in high yields via palladium-catalysed aminocarbonylation. The influence of the amine nucleophiles and of the reaction conditions on the isolated yields was investigated.

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Acknowledgments

The authors thank the Hungarian Scientific Research Fund (K113177) and Developing Competitiveness of Universities in the South Transdanubian Region (SROP-4.2.2.A-11/1/KONV-2012-0065) for the financial support and Johnson Matthey for the generous gift of palladium(II) acetate. The present scientific contribution is dedicated to the 650th anniversary of the foundation of the University of Pécs, Hungary.

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Authors and Affiliations

  1. Department of Inorganic Chemistry, University of Pécs and Szentágothai Research Centre, P.O. Box 266, Pecs, 7624, Hungary

    Roland Farkas & Andea Petz

  2. MTA-PTE Research Group for Selective Chemical Syntheses, Ifjúság u. 6., Pecs, 7624, Hungary

    László Kollár

Authors
  1. Roland Farkas
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  2. Andea Petz
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  3. László Kollár
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Correspondence to László Kollár.

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Farkas, R., Petz, A. & Kollár, L. Synthesis of 2-(1,4-dioxaspiro[4.5]decan-6-yl)acrylamides from 2-acetylcyclohexanone via palladium-catalysed aminocarbonylation. Monatsh Chem 146, 1665–1671 (2015). https://doi.org/10.1007/s00706-015-1535-3

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  • DOI: https://doi.org/10.1007/s00706-015-1535-3

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