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

Synlett

Volumn , Issue 15, 2003, Pages 2321-2324

  Matveeva, Elena D ^a   Podrugina, Tatyana A ^a   Tishkovskaya, Elena V ^a   Tomilova, Larisa G ^a   Zefirov, Nikolay S ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Catalysis; Ketones; Tetra tert butylphthalocyanines; aminophosphonates; aminophosphonic acids

Indexed keywords

3 METHYLCYCLOHEXANONE; ALPHA AMINO ACID; ALPHA AMINOPHOSPHONATE DERIVATIVE; AMMONIUM CARBONATE; AMMONIUM DERIVATIVE; BENZYLAMINE; CARBONIC ACID DERIVATIVE; CYCLOHEXANONE DERIVATIVE; DIETHYLPHOSPHITE; ESTER; KETONE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; PHTHALOCYANINE DERIVATIVE; TETRA TERT BUTYL PHTHALOCYANINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; KABACHNICK FIELDS REACTION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0346749669     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42118     Document Type: Article

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28. 2/MeOH = 20:1). In the case of steric hindered and cage ketones (adamantanone-2, camphor and norbornanone) 50% amine excess is required.
29. All obtained compounds gave satisfactory elemental analyses with the range of C ±0.3%, H ±0.2%, N ±0.3%.
30. -1 (C-O) in the IR spectra of given compounds. IR spectra of α-benzylaminophosphonates solutions were measured under the dilution forty times over. At that intensity and frequency the absorption bands of phosphonic and NH-associated groups did not change. This fact is evidence of the presence of intramolecular hydrogen bonds.
31. 31P NMR: δ = 30.53, 31.44 (2 s, 2:1) ppm.
32. PH = 3.1 Hz).
33. AB = 12.8 Hz).
34. 27