Syntézy 4-hydroxypyridin-2-onů s využitím alfa-aminonitrilů

Bc. Petra Hoffmannová

Master's thesis

Syntheses of 4-hydroxypyridin-2-ones Using Alfa-aminonitriles

Abstract:

Reakcí primárních aromatických aminů s methylketony a kyanovodíkem byly připraveny alfa-aminonitrily 1. Eliminací kyanovodíku byly alfa-aminonitrily 1 převedeny na iminy (anily) 2, které byly podrobeny kondenzaci s bis-(2,4,6-trichlorfenyl)estery kyseliny malonové za vzniku derivátů 4-hydroxypyridin-2(1H)-onů 3. Kondenzace byly provedeny jednak konvenční metodou A, jednak metodou asistovanou mikrovlnami B. Kondenzací iminu 2c s bis-(2,4,6-trichlorfenyl)-2-butylmalonátem 6a byl získán v závislosti na původu esteru 6a buď 3-butyl-4-hydroxy-1-(3-methoxyfenyl)-6-fenylpyridin-2(1H)-on 3b nebo 3-butyl-4-hydroxy-7-methoxychinolin-2(1H)-on 4b. Kondenzace iminu 2e s bis-(2,4,6-trichlorfenyl)-2-ethylmalonátem poskytla směs 1-(3,5-dimethylfenyl)-3-ethyl-4-hydroxy-6-fenylpyridin-2(1H)-onu 3g a 3-ethyl-4-hydroxy-5,7-dimethylchinolin-2(1H)-onu 4g.

Abstract:

By the reaction of aromatic amines with methylketones and hydrogen cyanide were prepared alpha-aminonitriles 1. By elimination of hydrogen cyanide were alpha-aminonitriles 2 transformed to imines, which were subjected to condensation with bis-(2,4,6-trichlorophenyl)esters of malonic acid to form 4-hydroxypyridin-2(1H)-one derivates 3. Condensations were provided by two methods, convinient method A and microwave method B. By condensation of imine 2c with bis-(2,4,6-trichlorophenyl)-2-butylmalonate 6a was obtained corresponding 3-butyl-4-hydroxy-1-(3-methoxyphenyl)-6-phenylpyridine-2(1H)-one 3b or 3-butyl-4-hydroxy-7-methoxychinoline-2(1H)-one 4b. By condensation of imine 2e with bis-(2,4,6-trichlorophenyl)-2-ethylmalonate was obtained mixture of 1-(3,5-dimethylphenyl)-3-ethyl-4-hydroxy-6-phenylpyridine-2(1H)-one 3g a 3-ethyl-4-hydroxy-5,7-dimethylchinoline-2(1H)-one 4g.

Keywords

syntéza, alfa-aminonitril, imin, 4-hydroxypyridin-2(1H)-on, bis-(2, 4, 6-trichlorfenyl)malonáty

Language used: Czech

Date on which the thesis was submitted / produced: 12. 5. 2023

Thesis defence

Tomas Bata University in Zlín

Faculty of Technology

Master programme / field:
Chemistry of Food and Bioactive Compounds / -