The kabachnik-fields and pudovik reactions on the basis of E,Z-citral and its imines and (R,S)-citronellal

Abstract

The Kabachnik-Fields reaction of E,Z-citral with diethyl phosphite in the presence of isobutylamine has been found to form α-aminophosphonates. The Pudovik reactions of diethyl phosphite with prenyl imines prepared on the basis of E,Z-citral with isobutylamine also allowed us to obtain the same α-aminophosphonates. We have managed to synthesize α- aminophosphonates by the reaction of O,O-dialkyl trimethylsilyl phosphites with prenyl imines in the presence of water or diethylamine. α- Aminophosphonates were also synthesized by the reaction of diethyl phosphite with (R,S)-citronellal in the presence of alkylamines. α-Aminophosphonates obtained showed bacteriostatic activity against Staphylococcus aureus and Bacillus cereus. © 2012 Wiley Periodicals, Inc.