Kabachnik-Fields Reaction

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Reaction [1]:

Mechanism [2]:

Example [3]:

Highlights and Significance:

  1. Microwave-assistant Kabachnik-Fields reaction could be used to synthesize aminomethylphosphonates. [4]
  2. Kabachnik-Fields reactions have a high activity and selectivity. [5]
  3. Kabachnik-Fields reaction is a simple method to prepare organophosphorus heterocycles. [6]

References:

  1. Keglevich, G.; Bálint, E., The Kabachnik-Fields reaction: Mechanism and synthetic use. Molecules 2012, 17 (11), 12821-12835.
  2. Villemin, D.; Didi, M. A., Aminomethylenephosphonic acids syntheses and applications (A Review). Orient. J. Chem. 2015, 31, 1-12.
  3. Tripolszky, A.; Zoboki, L.; Bálint, E.; Kóti, J.; Keglevich, G., Microwave-assisted synthesis of α-aminophosphine oxides by the Kabachnik-Fields reaction applying amides as the starting materials. Synth. Commun. 2019, 49 (8), 1047-1054.
  4. Mu, X.-J.; Lei, M.-Y.; Zou, J.-P.; Zhang, W., Microwave-assisted solvent-free and catalyst-free Kabachnik-Fields reactions for α-amino phosphonates. Tetrahedron Lett. 2006, 47 (7), 1125-1127.
  5. Rafael’A, C.; Galkin, V. I., The Kabachnik-Fields reaction: synthetic potential and the problem of the mechanism. Russ. Chem. Rev. 1998, 67 (10), 857-882.
  6. Qu, Z.; Chen, X.; Yuan, J.; Bai, Y.; Chen, T.; Qu, L.; Wang, F.; Li, X.; Zhao, Y., New synthetic methodology leading to a series of novel heterocyclic α-aminophosphonates: a very attractive expansion of Kabachnik-Fields reaction. Tetrahedron 2012, 68 (15), 3156-3159.