Application of Biginelli reaction to the synthesis of ferrocenylpyrimidones and [3]-ferrocenophane-containing pyrimido[4,5-d]pyrimidinediones

Facile synthesis and strong antiproliferative activity of disubstituted diphenylmethylidenyl-[3]ferrocenophanes on breast and prostate cancer cell lines

“…As part of our study on the antiproliferative effects of compounds based on the ferrocenyl-diphenyl-butadiene skeleton, we have recently shown that [3]ferrocenophane is an attractive pharmacophore in the development of cytotoxic agents for hormone-refractory breast cancer cells. 1,2 The ferrocenophane motif is found in a variety of compounds which have been used in catalysis, polymerization, sensors and electronics applications.…”

2,3-Dihydroferroceno[3,4]pyrrolo[2,1-b]thiazol-5(8b)-ones: Synthesis, Structure and DFT Study on the Mechanism of Chemo- and Diastereoslective Annulations of (Sp)-2-Formylferrocenecarbonyl Fluoride and (Sp)-2-Formylferrocenecarboxylic Acid

“…Scheme 2 ). Thus, after heating at reflux in acetic acid containing boric acid for 6 h, representing the conditions we have successfully used to promote Biginelli reactions [ 36 ] and Pictet-Spengler condensations [ 37 ], this amide was recovered a with retained structure in 54% yield from the reaction mixture by means of an aqueous workup. The resistance of 13 to cyclocondensation was rationalized by comparative DFT studies performed by B3PW91 functional [ 38 ] employing a DGTZVP basis set [ 39 ].…”

Synthesis of Pyrimidopyrimidinediones in a Deep Eutectic Reaction Mixture

“…Pyrimidopyrimidines are usually prepared from uracils 15. The synthesis of pyrimidopyrimidinediones has also been achieved by the reaction of urea, an aldehyde and ketone under acidic conditions using concentrated HCl,16a acetic acid/KHSO 4 16b and FeCl 3 ⋅6 H 2 O/TMSCl16c as catalysts.…”