31002-94-5

Upstream product

• 4471-09-4 N-benzylcyclohexylimine 
• 762-04-9 phosphonic acid diethyl ester 
• 108-94-1 cyclohexanone 
• 100-46-9 benzylamine 
• 762-04-9 Diethyl phosphonate 

Relevant academic research and scientific papers

Microwave-assisted one-pot synthesis of α-amino phosphonates via three component coupling on a silica gel support

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

A Novel Catalytic Three-Component Synthesis (Kabachnick-Fields Reaction) of α-Aminophosphonates from Ketones

A novel and highly convenient catalytic variant of the synthesis of α-aminophosphonates on basis of the Kabachnik-Fields reaction [three-component reaction of ketones, diethylphosphite and either benzylamine (series a) of ammonium carbonate (series b)] in the presence of tetra-tert-butylphthalocyanines has been developed. This method affords α-aminophosphonates in acceptable yields for various ketones, including cyclic, sterically hindered and cage ketones. The unsubstituted α-aminophosphonic acids were also obtained from the corresponding esters of series b.

Catalyst-free microwave-assisted synthesis of α-aminophosphonates in a three-component system: R1C(O)R2-(EtO) 2P(O)H-RNH2

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.

Diversity-oriented synthesis of α-aminophosphonates: A new class of potential anticancer agents

A small library of structurally diverse α-aminophosphonates has been synthesized by reacting alkyl/aryl aldehydes, alkyl/aryl amines and alkyl/aryl phosphites in one-pot catalyzed by Amberlite-IR 120 resin (acidic). All the synthesized a-aminophosphonates were assayed for their in vitro cytotoxic activities against a panel of five human cancer cell lines including A-549, NCI-H23 (Lung), Colo 320DM (Colon), MG-63 (Bone marrow) and Jurkat (Blood T lymphocytes). Compound 4n having (R)-1-phenylethanamine was found to be the most active amongst all the synthesized a-aminophosphonates against all the five cancer cell lines, most prominent being against Jurkat cell line with an IC 50 value of 4 μM. Surprisingly, compound 4o having (S)-1-phenylethanamine was found to be devoid of any cytotoxicity. Our finding suggests that these chemical entities could further serve as interesting template for the design of potential anticancer agents.

Zirconium(IV) compounds as efficient catalysts for synthesis of α-aminophosphonates

(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.

Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot

A simple, efficient, and environmentally benign method for a three-component reaction of an amine, an aldehyde or a ketone, and diethyl phosphite catalyzed by Amberlite-IR 120 resin has been developed to afford α-amino phosphonates in high yields and short reaction times under solvent-free reaction conditions. The major advantages of the present method are good yields, inexpensive, ecofriendly and reusable catalyst, mild and solvent-free reaction conditions and tolerance towards various functionalities present in the substrates.

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

(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.

Bismuth(III) chloride-catalyzed three-component coupling: Synthesis of α-amino phosphonates

A simple and efficient method has been developed for the one-pot synthesis of α-amino phosphonates from the reaction of a carbonyl compound, amine, and dialkyl phosphite. The highly catalytic nature of bismuth(III) chloride and the fact that it is relatively nontoxic, low cost, easy to handle, and insensitive to small amounts of air and moisture make this method especially attractive for large-scale synthesis. Copyright Taylor & Francis, Inc.

General procedure for the synthesis of α-amino phosphonates from aldehydes and ketones using indium(III) chloride as a catalyst

(matrix presented) (24 examples) A simple, efficient, and general method has been developed for the synthesis of α-amino phosphonates through a one-pot reaction of aldehydes and ketones with amines in the presence of indium(III) chloride as a catalyst.