Alkyl alkynylphosphonites in the Kabachnik-Fields reaction
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 wordsO-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
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