Journal ArticleDOI
Tandem addition of trialkyl phosphites to α,β-unsaturated imines : A comparison with silylated phosphites
TLDR
3-phosphonyl-1-aminophosphonates, phosphonic acid analogues of glutamate, are obtained in good yields in addition reactions to alpha,beta-unsaturated imines thanks to the steric bulk of the nitrogen substituent.Abstract:
Trialkyl phosphites were evaluated for addition reactions to α,β-unsaturated imines. An acidic medium is required to allow consecutive 1,4- and 1,2-addition to occur. In this manner, 3-phosphonyl-1-aminophosphonates, phosphonic acid analogues of glutamate, are obtained in good yields (32−90%). The reaction is mainly influenced by the steric bulk of the nitrogen substituent: less steric N-substituents lead to better yields of the tandem adducts.read more
Citations
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Journal ArticleDOI
1-(α-Aminobenzyl)-2-naphthol: A New Chiral Auxiliary for the Synthesis of Enantiopure α-Aminophosphonic Acids
Kirill E. Metlushka,Kirill E. Metlushka,Boris A. Kashemirov,V. F. Zheltukhin,D. N. Sadkova,Bernd Büchner,Christian Hess,Olga N. Kataeva,Charles E. McKenna,Vladimir A. Alfonsov +9 more
TL;DR: A new diastereoselective synthesis of alpha-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(alpha-aminobenzyl)-2-naphthol.
Journal ArticleDOI
Synthesis of new α-aminophosphonate derivatives incorporating benzimidazole, theophylline and adenine nucleobases using L-cysteine functionalized magnetic nanoparticles (LCMNP) as magnetic reusable catalyst: evaluation of their anticancer properties
Foroogh Bahrami,Farhad Panahi,Fatemeh Daneshgar,Reza Yousefi,Mohammad Bagher Shahsavani,Ali Khalafi-Nezhad +5 more
TL;DR: In this paper, a new class of structurally diverse α-aminophosphonate derivatives containing benzimidazole, theophylline and adenine heterocycles were synthesized using a simple and efficient strategy.
Journal ArticleDOI
One-pot tandem 1,4–1,2-addition of phosphites to quinolines
Ann De Blieck,Kurt G. R. Masschelein,Frederic Dhaene,Ewa Rozycka-Sokolowska,Bernard Marciniak,Józef Drabowicz,Christian V. Stevens +6 more
TL;DR: Trialkyl and silylated dialkyl phosphites were evaluated as phosphorus nucleophiles for the addition to quinolines in a strong acidic medium allowing consecutive 1,4- and 1,2-addition breaking up the aromatic stabilisation, thereby leading to 2, 4-diphosphono-1,2,3,4 -tetrahydroquinoline addition in one single reaction step in moderate to good yields.
Journal ArticleDOI
Asymmetric Conjugate Addition of Malonate Esters to α,β‐Unsaturated N‐Sulfonyl Imines: An Expeditious Route to Chiral δ‐Aminoesters and Piperidones
TL;DR: The asymmetric conjugate addition of malonate esters to α,β-unsaturated N-sulfonyl imines is catalyzed by PyBOX/La(OTf)3 complexes in the presence of 4 Å MS to provide a synthetic entry to chiral δ-aminoesters and piperidones.
Journal ArticleDOI
Direct diphosphonylation of quinolines with H-phosphonates under metal-free conditions
TL;DR: In this paper, the synthesis of 2,4-diphosphono-1,2,3,4tetrahydroquinolines starting from quinolines and H-phosphonates has been developed.
References
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Journal ArticleDOI
Signal transduction, pharmacological properties, and expression patterns of two rat metabotropic glutamate receptors, mGluR3 and mGluR4
TL;DR: In this article, the authors studied the signal transduction mechanism and pharmacological characteristics of the rat mGluR3 and mgluR4 subtypes in Chinese hamster ovary cells permanently expressing the cloned receptors.
Journal ArticleDOI
General Procedure for the Synthesis of α-Amino Phosphonates from Aldehydes and Ketones Using Indium(III) Chloride as a Catalyst
TL;DR: In this article, a simple, efficient, and general method was 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.
Journal ArticleDOI
Three component coupling catalyzed by TaCl5–SiO2: synthesis of α-amino phosphonates
TL;DR: TaCl5−SiO2 has been used as an efficient Lewis acid catalyst for the three component coupling of carbonyl compounds, aromatic amines and diethyl phosphite to produce α-amino phosphonates as discussed by the authors.
Journal ArticleDOI
Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions
Babak Kaboudin,Rahman Nazari +1 more
TL;DR: In this article, a simple, efficient and general method was developed for the synthesis of 1-aminoalkyl phosphonates through a one-pot reaction of aldehydes with amines in the presence of acidic alumina under solvent-free conditions using microwave irradiation.
Journal ArticleDOI
Lithium perchlorate/diethylether catalyzed aminophosphonation of aldehydes
TL;DR: In this paper, a simple and efficient one-pot method was developed to give α-aminonitriles from aldehydes + amines + TMSCN in LPDE.