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. Heteroatom Chem 24:36–42, 2013; View this article online at http://wileyonlinelibrary.com. DOI 10.1002/hc.21060

6. Synthesis of α-aminophosphonates by the Kabachnik–Fields reaction and by the Pudovik reaction

“…An imine derived from furan-3-carbaldehyde and propargyl amine was converted to an aminophosphonate by a hydrophosphonylation reaction with dimethyl phosphite. The catalyst-and solvent-free addition was complete at 60 °C after 8 h ( Figure 6 A terpene-type Schiff base was converted to an α-aminophosphonate by reaction with diethyl phosphite at 20 °C for 2 h (Figure 6.68) [132].…”

Synthesis of Biologically Active α-Aminophosphonates

“…Nizamov et al [29] have been synthesized O,Odiethyl -(N-isobutylamino)-3,7-dimethylocta-2,6dienylphosphonates (10) in two methods. Method A was the Kabachnik-Fields reaction of E,Z-citral (9) with diethyl phosphite in the presence of isobutylamine to form -aminophosphonates (Scheme 5).…”

“…Method B was the Pudovik reaction of diethyl phosphite with i-butyl imines (9a) prepared on the basis of E,Z-citral with isobutylamine to obtain the same aminophosphonates (Scheme 6). O,O-diethyl -(Namino)-3,7-dimethylocta-6-enylphosphonates (12a,b) were also synthesized [29] from isobutyl/isopropyl amine, diethyl phosphite and (R,S)-citronellal (11) (Scheme 7). These -aminophosphonate derivatives exhibited bacteriostatic activity [29] against Staphylococcus aureus and Bacillus cereus.…”