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1.
Molecules ; 27(22)2022 Nov 09.
Article in English | MEDLINE | ID: mdl-36431787

ABSTRACT

A series of new symmetrical 2,5-dialkyl-1,3,4-oxadiazoles containing substituted alkyl groups at the terminal positions with substituents, such as bromine, isopropyloxycarbonylmethylamino, and carboxymethylamino, were successfully synthesized. The developed multistep method employed commercially available acid chlorides differing in alkyl chain length and terminal substituent, hydrazine hydrate, and phosphorus oxychloride. The intermediate bromine-containing 2,5-dialkyl-1,3,4-oxadiazoles were easily substituted with diisopropyl iminodiacetate, followed by hydrolysis in aqueous methanol solution giving the corresponding 1,3,4-oxadiazoles bearing carboxymethylamino substituents. The structure of all products was confirmed by conventional spectroscopic methods including 1H NMR, 13C NMR, and HRMS.


Subject(s)
Bromine , Oxadiazoles , Oxadiazoles/chemistry , Magnetic Resonance Spectroscopy
2.
Molecules ; 25(12)2020 Jun 18.
Article in English | MEDLINE | ID: mdl-32570910

ABSTRACT

Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, N,N-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by 1H-NMR, 13C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed.


Subject(s)
Azo Compounds/chemistry , Azo Compounds/chemical synthesis , Thiadiazoles/chemistry , Models, Molecular , Molecular Structure , Spectrophotometry, Ultraviolet
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