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An efficient one-pot synthesis of 1-aminophosphonates

Kaboudin, B ; Sharif University of Technology | 2022

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  1. Type of Document: Article
  2. DOI: 10.1055/a-1941-1242
  3. Publisher: Georg Thieme Verlag , 2022
  4. Abstract:
  5. 1-Aminophosphonates are valuable compounds with wide range of applications in biological and industry. Various reaction conditions and catalysts have been reported for the synthesis of 1-aminophosphonates via three-component (dialkyl phosphite + aldehyde + amine) or two-component reaction (dialkyl phosphite + imine). Here a solvent-free synthesis of 1-aminophosphonates under very mild reaction conditions is reported. The three-component condensation reactions of dialkyl phosphite, carbonyl compound, and an amine gave 1- aminophosphonates in good to excellent yields under solvent- and catalyst-free conditions at ambient temperature. Hydrophosphorylation of imines in the presence of dialkyl phosphite under the same conditions gave also 1-aminophosphonates in good to excellent yields. These results showed that the reaction needs no catalyst or solvent for activation. It seems a tautomeric form of dialkyl phosphite (as one of the components) catalyzed the reaction. The reaction yield decreased using any solvent. In addition, a novel method is reported for the synthesis of N-deprotected 1-aminophosphonates (analogues of 1-amino acids) from N-PMP 1-aminophosphonate in the presence of TCCA. To understand the activity of the dialkyl phosphite under solvent-free conditions, the DFT calculations have provided insight into the basis of this activity. © 2022 Georg Thieme Verlag. All rights reserved
  6. Keywords:
  7. Aminophosphonates ; Dialkyl phosphite ; Free aminophosphonates ; Imine ; Carbonyl compounds ; Catalysts ; Condensation reactions ; Aminophosphonates ; Amiophosphonate ; Condition ; Dialkyl phosphite ; Dialkylphosphite ; Freeaminophosphonate ; Imine ; Solvent free ; Three-component ; ]+ catalyst ; Solvents ; 1 aminophosphonate ; Amine ; Carbonyl derivative ; Cyanuric acid ; Diethyl (1 aminocyclohexyl)phosphonate ; Diethyl [(2 hydroxyphenyl)(phenylamino)methyl]phosphonate ; Diethyl [(2,4 dichlorophenyl)(phenylamino)methyl]phosphonate ; Diethyl [(2,6 dichlorophenyl)(phenylamino)methyl]phosphonate ; Diethyl [(4 fluorophenyl)(phenylamino)methyl]phosphonate ; Diethyl [(4 methoxyphenyl)(phenylamino)methyl]phosphonate ; Diethyl [(4 nitrophenyl)(phenylamino)methyl]phosphonate ; Diethyl [(4 phenoxyphenyl)(phenylamino)methyl]phosphonate ; Diethyl [1 (benzylamino)cyclohexyl]phosphonate ; Diethyl [1 (phenylamino)octadec 9 en 1 yl]phosphonate ; Diethyl [1 [(4 methoxyphenyl)amino]cyclohexyl]phosphonate ; Diethyl [2 (phenylamino)octan 2 yl]phosphonate ; Diethyl [3 phenyl 1 (4 tolylamino)allyl]phosphonate ; Diethyl [[(4 methoxyphenyl)amino](phenyl)methyl]phosphonate ; Diethyl [[4 (methylthio)phenyl](phenylamino)methyl]phosphonate ; Diethyl [[4 (octadec 9 en 1 yloxy)phenyl](phenylamino)methyl]phosphonate ; Diethyl [[[3 (1h imidazol 1 yl)propyl]amino] (1 trityl 1h imidazol 4 yl)methyl]phosphonate ; Diethyl[(benzylamino) (1 trityl 1h imidazol 4 yl)methyl]phosphonate ; Diethyl[(benzylamino) (4 nitrophenyl)methyl]phosphonate ; Diethyl[(benzylamino)(phenyl)methyl]phosphonate ; Diethyl[(cyclohexylamino) (4 nitrophenyl)methyl]phosphonate ; Diethyl[(cyclohexylamino) (4 tolyl)methyl]phosphonate ; Diethyl[(cyclohexylamino)(phenyl)methyl]phosphonate ; Diethyl[(phenylamino) (4 tolyl)methyl]phosphonate ; Diethyl[amino(phenyl)methyl]phosphonate ; Diethyl[naphthalen 2 yl(phenylamino)methyl]phosphonate ; Diethyl[phenyl(phenylamino)methyl]phosphonate ; Diisopropyl [1 (phenylamino)cyclohexyl]phosphonate ; Diisopropyl[phenyl(phenylamino)methyl]phosphonate ; Diphenyl[(phenylamino) (4 tolyl)methyl]phosphonate ; Diphenyl[phenyl(phenylamino)methyl]phosphonate ; Imine ; Phosphite ; Phosphonic acid derivative ; Trichloroisocyanuric acid ; Unclassified drug ; Catalyst ; Deprotection reaction ; Hydrophosphorylation ; Nucleophilicity ; One pot synthesis ; Phosphorylation ; Polymerization ; Reaction temperature ; Tautomer
  8. Source: Synthesis (Germany) ; Volume 55, Issue 1 , Volume 55, Issue 1 , 2022 , Pages 121-130 ; 00397881 (ISSN)
  9. URL: https://www.thieme-connect.com/products/ejournals/abstract/10.1055/a-1941-1242