19555-24-9Relevant academic research and scientific papers
An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate
Bhagat, Srikant,Chakraborti, Asit K.
, p. 1263 - 1270 (2007)
(Chemical Equation Presented) Commercially available magnesium perchlorate is reported as an extremely efficient catalyst for the synthesis of α-aminophosphonates. A three-component reaction (3-CR) of an amine, an aldehyde or a ketone, and a di-/trialkyl phosphite (Kabachnik-Fields reaction) took place in one pot under solvent-free conditions to afford the corresponding α-aminophosphonates in high yields and short times. The use of solvent retards the rate of the reaction and requires a much longer reaction time than that for neat conditions. The reactions involving an aldehyde, an aromatic amine without any electron-withdrawing substituent, and a phosphite are carried out at rt. The reactions involving cyclic ketones, aromatic amines with an electron-withdrawing substituent, and aryl alkyl ketone (e.g., acetophenone) require longer reaction times at rt or heating. Magnesium perchlorate was found to be superior to other metal perchlorates and metal triflates during the reaction of 4-methoxybenzaldehyde, 2,4-dinitroaniline, and dimethyl phosphite. The catalytic activity of various magnesium compounds was influenced by the counteranion, and magnesium perchlorate was found to be the most effective. The reaction was found to be general with di-/trialkyl phosphites and diaryl phosphite. The Mg(ClO4)2-catalyzed α- aminophosphonate synthesis in the present study perhaps represents a true three-component reaction as no intermediate formation of either an imine or α-hydroxy phosphonate was observed that indicated the simultaneous involvement of the carbonyl compound, the amine, and the phosphite in the transition state.
New one-pot three-component synthesis of N-phenyl α-aminophosphonates
Deng, Sheng-Lou,Dong, He-Chao
, p. 3411 - 3417 (2006)
New one-pot three-component reactions employing aldehydes, triphenylphosphite, and N-[(phenylamino)carbonyl]glycine ethyl ester in refluxing xylene readily afford N-phenyl α-aminophosphonates in low to moderate yields. Copyright Taylor & Francis Group, LL
Zinc Di(l-prolinate)-Mediated Synthesis of α-Aminophosphonates under Mild Conditions
De Oliveira, Aline R.,Katla, Ramesh,Rocha, Mariana P. D.,Albuquerque, Tábata B.,Da Silva, Caren D. G.,Kupfer, Vicente L.,Rinaldi, Andrelson W.,Domingues, Nelson Luís Campos
, p. 4489 - 4494 (2016/12/16)
An efficient method has been developed for the preparation of α-aminophosphonates by using zinc di(l-prolinate) as a catalyst under mild reaction conditions. The method has the advantages of high yields, short reaction times, and easy workup conditions.
A new, efficient and recyclable [Ce(l-Pro)]2(Oxa) heterogeneous catalyst used in the Kabachnik-Fields reaction
Da Silva, Caren D. G.,Oliveira, Aline R.,Rocha, Mariana P. D.,Katla, Ramesh,Botero, Eriton Rodrigo,Da Silva, érica C.,Domingues, Nelson Luís C.
, p. 27213 - 27219 (2016/03/25)
Herein we introduce a new catalyst for the Kabachnik-Fields reaction, [Ce(l-Pro)]2(Oxa), using a very accessible, simple and efficient methodology for α-aminophosphonate synthesis using an aromatic aldehyde, an aromatic amine and diphenyl phosphite. This procedure was developed using a low catalyst loading of cerium(iii) prolinate and it has allowed for the recycling of the catalyst.
Iron-doped single walled carbon nanotubes as an efficient and reusable heterogeneous catalyst for the synthesis of organophosphorus compounds under solvent-free conditions
Sharghi, Hashem,Ebrahimpourmoghaddam, Sakineh,Doroodmand, Mohammad Mahdi
, p. 4708 - 4724 (2013/06/26)
Iron-doped single walled carbon nanotubes (Fe/SWCNTs) is an efficient, eco-friendly, and reusable heterogeneous catalyst for the synthesis of diversely decorated α-aminophosphonates via multicomponent reaction of amines, carbonyl compounds, and phosphorus compounds under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines and carbonyl compounds. It also enabled the development of one-pot synthesis of β-phosphonomalonates during the reaction of carbonyl compounds, malononitrile and phosphorus compounds. Excellent results were obtained in each case affording the corresponding organophosphorus adducts in good yields.
Zirconium(IV) compounds as efficient catalysts for synthesis of α-aminophosphonates
Bhagat, Srikant,Chakraborti, Asit K.
, p. 6029 - 6032 (2008/12/21)
(Chemical Equation Presented) Zirconium(IV) compounds are reported as excellent catalysts for a three-component one-pot reaction of an amine, an aldehyde or a ketone, and a di/trialkyl/aryl phosphite to form α-aminophosphonates under solvent-free conditions at rt. Among the various zirconium compounds, ZrOCl2?8H2O and ZrO(ClO 4)2?6H2O were most effective. The reactions were faster with dialkyl/diaryl phosphites than with trialkyl/triaryl phosphites. No O-Me cleavage occurs with aryl methyl ether and methyl ester groups. α/β-Unsaturated carbonyl moiety does not undergo conjugate addition with the phorphorous moiety.
