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Synteza estrów kwasu fosfonooctowego i ich praktyczne zastosowanie w otrzymywaniu fosforylowanych kumaryn

Frynas Sławomir, Szwaczko Katarzyna, Dziuba Kamil

Przemysł Chemiczny

2023

T. 102, nr 1

73--76

Estry kwasu fosfonooctowego 1 (R¹ = R² = Me, Et, i-Pr, R³ = Et, i-Pr, PhCH₂, Ph) otrzymano w reakcji Michaelisa i Arbuzowa fosforynów alkilowych z estrami kwasu bromoctowego. Reakcje przeprowadzono bez rozpuszczalnika w temp. 80-110°C. Otrzymane estry 1 użyto następnie w reakcji z aldehydem salicylowym w obecności katalizatora (pirolidyna i MeCOOH), uzyskując fosforylowane kumaryny 2 (R = Me, Et, i-Pr) z prawie całkowitą konwersją i wysokimi wydajnościami wydzielonego produktu, wynoszącymi 75-85%.

Phosphonoacetic acid esters 1 (R¹ = R² = Me, Et, i-Pr, R³ = Et, i-Pr, PhCH₂, Ph) were obtained via Michaelis-Arbuzov reaction of alkyl phosphites with bromoacetates, carried out without solvent at 80-110°C. Treatment of 1 with salicylaldehyde in the presence of a catalyst (pyrrolidine and acetic acid) gave phosphorylated coumarins 2 (R = Me, Et, i-Pr) with almost complete conversion and high isolated yields up to 75-85%.

Through Knoevenagel synthesis of coumarines to methcrylate monomers containing optical active groups

Bogdał D., Stępień I., Pajda M.

Polish Journal of Chemical Technology

2003

Vol. 5, nr 3

90-92

Coumarines are compounds originating from the nature, used in many areas such as cosmetics, seasonings, pharmaceutics, and photochemistry. There are many developed methods of coumarines synthesis, e.g. Pechman reaction, Perkin reaction, Knoevenagel condensation and many others. Since coumarine derivatives have been studied in our laboratory, we have investigated their synthesis through Knoevenagel condensation. 3-carboxycoumarines were synthesized from appropriate hydroxybenzealdehydes and then their methacrylate monomers were synthetised using 2-hydroxyethyl methacrylate. All compounds were identified by GC-MS and IR and gave satisfactory results in comparison with authentic samples. Described in this paper series of monomers were copolymerised with other monomers to give photo- and electroluminescent copolymers.