Povarov Reaction

Povarov Reaction

11 March, 2016 / by / in Reactions
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  • Generality
  • Reagent Availability
  • Experimental User Friendliness

  • General Characteristics

The condensation of aldehydes, anilines, and electron-rich alkenes provides access to substituted tetrahydroquinoline skeletons. This is a type of three-component reaction involving hetero Diels-Alder cycloaddition. Tetrahydroquinolines can be oxidized to quinolines if needed.

  • General References

  • Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1963, 953.
  • Povarov, L. S.; Grigos, V. I.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1963, 2039.
  • Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656.
  • Buonora, P.; Olsenb, J.-C.; Oh, T. Tetrahedron 2001, 57, 6099. doi:10.1016/S0040-4020(01)00438-0
  • Kouznetsov, V. V. Tetrahedron 2009, 65, 2721. doi:10.1016/j.tet.2008.12.059
  • Bello, D.; Ramon, R.; Lavilla, R. Curr. Org. Chem. 2010, 14, 332.

  • Reaction Mechanism

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  • Examples

The synthesis of unsymmetrical phenanthrolines.[1]

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The application to the synthesis of camptothecin.[2]

Povarov_4.gif

  • Experimental Tips

  • References

[1] De, K.; Legros, J.; Crousse, B.; Chandrasekaran, S.; Bonnet-Delpon, D. Org. Biomol. Chem. 2011, 9, 347. DOI: 10.1039/C0OB00496K
[2] Twin, H.; Batey, R. A. Org. Lett. 2004, 6, 4913. DOI: 10.1021/ol0479848

  • Related Reactions

  • Related Books

  • External Links

Povarov Reaction – Wikipedia

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