Synthesis of heterocyclic methylenebisphosphonates by 1,3-dipolar cycloaddition of ethyl diazoacetate to 1,2-benzoxaphosphorin-3-phosphonates

Synthesis of Tetrazoloquinoline‐Based Mono‐ and Bisphosphonate Esters as Potent Anti‐Inflammatory Agents

“…The formation of 14a , 14b can be rationalized as occurring in Scheme through the condensation of 13 with the aldehydic‐carbonyl group and extrusion of a molecule of H 2 O (Perkin‐type condensation). Perkin reaction has been previously described for a similar reaction of the bisphosphonate 13 with aldehydes . Ethylidenebis‐phosphonates and the relevant phosphonic acids belong to an important class of compounds used for the treatment of bone diseases, such as osteoporosis, hypocalcemia, inflammation, and rheumatoid arthritis .…”

Synthesis and Chemical Properties of 3-Phosphono-coumarins and 1,2-Benzoxaphosphorins as Precursors for Bioactive Compounds

“…A synthetic protocol including the formation of dialkyl 1,2-benzoxaphosphorin-3-phosphonates 55a – f [64] under Knoevenagel reaction conditions (Scheme 37) was performed by using substituted salicylaldehydes 3a – c , e , i , k and tetraethyl methylenebisphosphonate ( 7d ). The products 55a – f were isolated in yields from 69 to 92%.…”

“…Pyrazoline derivatives of 3-diethylphosphonocoumarin 80a , b , 1,2-benzoxa- phosphorine-3-carboxylates and 1,2-benzoxaphosphorin-3-phosphonates 81 were prepared [64] in reactions with ethyl diazoacetate. The solvent mixture for the three coumarins was different based on their solubility and the solubility of the products.…”

Crystal Structure and Spectroscopic Properties of (2-oxo-2H-chromen-3-yl)phosphonic Acid Monoethyl Ester Trihydrate

“…On the other hand, the predicted values of ν P O , ν as PO2 , and ν s PO2 stretching vibrations differ by 15-22 cm −1 . This result can be explained Table 4 Data of the ν i and A i of the IR-bands within 1300-800 cm −1 region obtained by preliminary deconvolution and curve-fitting procedure ( Figure 5) 5 3.9395 1039.4 6 14.8168 1251.5 8 3.1047 1012.4 4 14.4514 1211.0 8 6.9970 987.3 7 12.5481 1172.5 1 12.9694 950.7 3 12.8425 1133.9 6 10.3541 917.9 5 5.81360 1101.1 6 8.16931 883.2 3 1.36457 1110.7 9 7.73644 863.9 5 .2636 by the participation of the discussed functional groups in hydrogen bond interactions in the solid-state (Table 3). Similar results are obtained for the correlation between the theoretical and experimental values also for other derivatives.…”

“…1,2 As a part of our systematic study on the synthesis, 3-10 spectroscopic, and structural characterization of novel coumarins, [8][9][10] their salts, and metal complexes [11][12][13][14][15][16][17][18] with potential biological activity, [1][2][3][4][5] we are presenting here the crystal structure and spectroscopic properties of novel (2-oxo-2H-chromen-3-yl)phosphonic acid monoethyl ester trihydrate, shown in Figure 1.…”