Russian Chemical Bulletin

, Volume 47, Issue 10, pp 2047–2048 | Cite as

Alkyl alkynylphosphonites in the Kabachnik-Fields reaction

  • Yu. G. Trishin
  • V. I. Maslov
Brief Communications

Abstract

O-Ethyl alkynylphosphonites [EtOP(O)(H)CэCR] (1 and2) react withp-bromobenzaldehyde and benzylamine to form the usual acyclic products of the Kabachnik-Fields reaction or phosphorus-containing heterocycles depending on the nature of the substituent R at the β-carbon atom of the acetylene fragment of phosphonite. In the case of R=But,O-ethyl (α-benzylamino-p-bromobenzyl)(3,3-dimethylbut-1-ynyl)phosphinate (3) was obtained. In the case of R=Me, 1-benzyl-2-p-bromophenyl-3-ethoxy-5-methyl-3-oxo-Δ4-1,3-λ5-azaphospholine (4) was formed. Compounds3 and4 were also synthesized by the reactions of the above-mentioned phosphonites with the corresponding azomethines.

Key words

O-alkyl alkynylphosphonites Kabachnik-Fields reaction O-ethyl (α-benzylamino-p-bromobenzyl)(3,3-dimethylbut-1-ynyl)phospinate I-benzyl-2-p-bromophenyl-3-ethoxy-5-methyl-3-oxo-Δ4-1,3-λ5-azaphospholine synthesis IR and NMR spectra 

References

  1. 1.
    M. I. Kabachnik and T. Ya. Medved',Dokl. Akad. Nauk SSSR [Dokl. Chem.], 1952,83, 689; 1952,84, 717 (in Russian); E. K. Fields,J. Am. Chem. Soc., 1952,74, 1528.Google Scholar
  2. 2.
    E. E. Nifant'ev,Khimiya gidrofosforil'nykh soedinenii [Chemistry of Hydrophosphoryl Compounds], Nauka, Moscow, 1983, 264 pp. (in Russian).Google Scholar
  3. 3.
    Yu. G. Trishin, B. F. Mingazova, and I. V. Konovalova,Zh. Obshch. Khim., 1995,65, 161 [J. Gen. Chem. USSR, 1995,65 (Engl. Transl.)].Google Scholar

Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • Yu. G. Trishin
    • 1
  • V. I. Maslov
    • 1
  1. 1.St. Petersburg State Technological University of Plant PolymersSt. PetersburgRussian Federation

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