Synthesis and NMR Spectroscopic Study of New Furan-Derived Bis(Aminophosphonates)

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 182; no. 1; pp. 57 - 64
• Main Authors: Kraicheva, I., Finocchiaro, P., Failla, S.
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis Group 01.01.2007; Taylor & Francis
• Subjects: Aminophosphonic acids; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; furan derivatives; NMR spectra; Physical Sciences; Schiff bases; Science & Technology; Schiff bases; ALPHA-AMINO; ACID; furan derivatives; ADDITION-PRODUCTS; BISPHOSPHONATES; THERAPY; aminophosphonic acids; NMR spectra; C-13 NMR; PHOSPHITES; SPECTRA; DERIVATIVES
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426500600866903

The synthesis of two novel furyl-containing bis(aminophosphonates) 1,5-bis[N-methyl(dimethoxyphosphonyl)-1-(2-furyl)]diaminonaphthalene (1) and 1,5-bis[N-methyl(diethoxyphosphonyl)-1-(2-furyl)]diaminonaphthalene (2) through an addition of dialkyl phosphites to N,N′-difurfurylidene-1,5-naphthalenediamine is reported. The compounds have been characterized by elemental analysis, TLC, IR and NMR ( 1 H, 1 C and 31 P) spectra. Some new 31 P NMR data of three previously described analogues (3-5) of the above bis(aminophosphonates) is also presented. The 31 P NMR study reveals that in most of the cases (1, 3-5), the addition reaction is completely stereoselective, and only one diastereomer is formed. By the preparation of compound 2, this reaction proceeds not completely stereoselectively with the predominant formation (in 90%) of one of the two possible diastereomers.