31002-94-5Relevant articles and documents
Microwave-assisted one-pot synthesis of α-amino phosphonates via three component coupling on a silica gel support
Zhan, Zhuang-Ping,Yang, Rui-Feng,Li, Jun-Ping
, p. 1042 - 1043 (2005)
A fast, highly efficient, general procedure under microwave irradiation, using silica gel-supported reagents for the synthesis of α- aminophosphonates is developed through a one-pot reaction of aldehydes and ketones with amines. Copyright
Catalyst-free microwave-assisted synthesis of α-aminophosphonates in a three-component system: R1C(O)R2-(EtO) 2P(O)H-RNH2
Kabachnik, Maria M.,Zobnina, Elena V.,Beletskaya, Irina P.
, p. 1393 - 1396 (2005)
An effective catalyst-free microwave-assisted synthesis of α-aminophosphonates from ketones in a three-component system was shown. The method affords α-aminophosphonates in high yields from various ketones including natural porphyrine derivatives. Georg Thieme Verlag Stuttgart.
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.
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 (2007/10/03)
(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.
