Bazı 3-alkil (aril)-4-alkiliden (ariliden) amino-ve 3-alkil (aril)-4 alkil (aril) amino-4,5-dihidro-1H-1,2,4-triazol-5-on bileşiklerinin sentezi ve özelliklerinin incelenmesi
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Abstract
ÖZET Bu çalışmada önce bazı 3-Alkil(Aril)-4-Amino-4,5-Dihidro-lH-l,2,4-Triazol-5-on bileşikleri sentezlenmiş ve ayrı ayrı kapron aldehid, siklohekzan karboksaldehid, tarçın aldehid, fenilasetaldehid ve 1-naftaldehid ile muamele edilmek suretiyle 3-Alkil(Aril)-4- Alkiliden(Ariliden)Amino-4,5-Dihidro-lH-l,2,4-Triazol-5-on bileşikleri elde edilmiştir. Elde edilen ve birer schiff bazı karakterinde olan bu bileşiklerin içinden örnek olarak seçi lenler asetik anhidrid ile muamele edilmek suretiyle N-asetil türevlerine dönüştürülmüştür. 3-Alkil(Aril)-4-Alkil(Aril)Amino-4,5-Dihidro-lH-l,2,4-Triazol-5-on bileşiklerinin sentezi ise çalışmada elde edilen yeni schiff bazlarının azometin grubunun indirgenmesi yoluyla gerçekleştirilmiştir. Bunlara ek olarak çalışmada elde edilen 3-Alkil(Aril)-4-(l-naftilmetilamino)-4,5- Dihidro-lH-l,2,4-Triazol-5-on bileşiklerinin asetik anhidrid ile muamelesi incelenmiş ve çeşitli mono- ve disaetil türevleri elde edilmiştir. Çalışmada elde edilen 65 yeni bileşiğin yapı aydınlatılmaları mikroanaliz, İR, !H- NMR, 13C-NMR ve UV spektroskopisi yöntemleri ile yapılmıştır ve çalışmada uygulanan reaksiyonlar için reaksiyon mekanizmaları önerilmiştir. Anahtar Kelimeler : 1,2, 4-Triazol'ler, 4,5-Dihidro-lH-l,2,4-Triazol-5-on'lar, Schiff bazları, Azometin grubu, Aldehidler, İndirgenme, Nükleofilik katılma. V SUMMARY Synthesis of Some 3-AIkyl(Aryl)-4-Alkylidene(Arylidene)amino- and 3-Alkyl(Aryl)-4- Alkyl(Aryl)amino-4,5-Dihydro-lH-l,2,4-Triazol-5-Ones and Investigation of Their Properties. In this study initially, some 3-alkyl(aryl)-4-amino-4,5-dihydro-lH-l,2,4-triazol-5- ones were synthesized and subsequently, by the reaction of there compounds with various aldehydes such as capronaldehide, cyclohexane carboxaldehyde, cinnamaldehyde, phenylacetaldehyde and 1-naphaldehyde, 3-alkyl(aryl)-4-alkylidene(arylidene)amino-4,5- dihydro-lH-l,2,4-triazol-5-ones were obtained. Some selected compounds carrying schiff base character were converted to their acetyl derivatives by treating with acetic anhydride. The synthesis of some 3-alkyl(aryl)-4-alkyl(aryl)amino-4,5-dihydro-lH- 1,2,4- triazol-5-ones were succeeded by the NaBHU- reduction of azomethine groups of the bases obtained. Furthermore, the reaction of the new 3-alkyl(aryl)-4-(l-naphtymethylamino)-4,5- dihydro-lH-l,2,4-triazol-5-ones with acetic anhidride was investigated and their mono- or diacetyl derivatives were characterized. The structures of 65 new compounds synthesized in this study were proposed by evoluating the data obtained by microanalyses and spectroscopic methods such as IR, 'H- NMR, C-NMR. Some physical properties of these compounds were determined and their UV spectra were recorded. Moreover, reaction mechanisms were proposed for the general methods established in the study. Keywords : 1,2,4-Triazoles, 4,5-Dihydro-lH-l,2,4-triazol-5-ones, Schiff bases, Azomethine group, Aldehydes, Nucleophilic addition. VI
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