Çeşitli oksadiazin-5-on, oksadiazin-6-on ve ilgili bileşiklerin sentezi
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Date
1998-06-18
Authors
Arıkan, Nevin
Journal Title
Journal ISSN
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Publisher
Uludağ Üniversitesi
Abstract
Bu çalışmada, piridin hidroksamik asit klorürü hidroklorürlerinin primer aminlerle reaksiyonundan bazı yeni N-sübstitüe piridin karboksamid oksimler elde edildiler. Trietilamin beraberinde amidoksimlerin klorasetil klorür ile reaksiyonu karşılık gelen 3,4-disübstitüe-1,2,4-oksadiazin-5-onları verdi. 3,4- Disübstitüe-1,2,4-oksadiazin-5-tiyonlar, oksadiazin-5-onların fosfor penta sülfürle reaksiyonundan iyi verimlerle elde edildiler. 3,5-Disübstitüe-1,2,4-oksadiazin-6-onlar, a-amino asid ester hidroklorürlerinin piridin hidroksamik asid klorürü hidroklorürleri ile reaksiyonundan elde edildiler. Öte yandan, 2-oksoalkanoik asid açilhidrazonlarının DCC ile reaksiyonundan 2,5-disübstitüe1,3,4-oksadiazin-6-on bileşikleri elde edildiler. 3,4-Disübstitüe-A2-1,2,4-oksadiazolin-5-tiyonların karşılık gelen 3,4-disübstitüe A2-1,2,4-tiyadiazolin-5-onlara çevrildikleri daha önceden gösterilmişti. Benzer çevrilme için oksadiazin-6-onların fosfor pentasülfürle reaksiyonundan oksadiazin-6-tiyonları elde etmek istedik. Ancak reaksiyon gerçekleşmedi, oksadiazin-6-on bileşiklerinin değişmeden kaldığı veya bozunduğu belirlendi. Oksadiazin-5-onların, oksadiazin-5-tiyonların ve oksadiazin-6-onların anti- mikrobiyal aktiflikleri araştırıldı ve oldukça iyi antimikrobiyal aktifliğe sahip oldukları saptandı.
In this study some new N-substituted pyridine carboxamide oximes are obtained from the reactions of pyridine hydroxamic acid chloride hydrochlorides with primary amines. The reactions of carboxamide oximes with chloroacetyl chloride in the presence of triethylamine gave the corresponding 3,4- disubstituted-1,2,4-oxadiazin-5-ones. 3,4-Disubstituted-1,2,4-oxadiazin -5- thiones are prepared in good yields by the reactions of 3,4-disubstituted-1,2,4- oxadiazin-5-ones and phosphorus pentasulphide. 3,5-Disubstituted-1,2,4-oxadiazin-6-ones are prepared by the reactions of a- amino acid ester hydrochlorides with pyridine hydroxamic acid chloride hydrochlorides. On the other hand, 2,5-disubstituted-1,3,4-oxadiazin-6-ones are obtained from the reactions of 2-oxoalkanoic acid acylhydrazones and DCC. We have previously shown that 3,4-disubstituted A2-1,2,4-oxadiazolin-5-thiones rearranged to the corresponding 3,4-disubstituted A2-1,2,4-thiadiazolin-5-ones. For the similar rearrangement we have attempted to prepare oxadiazin-6- thiones from the oxadiazin-6-ones, using phosphorus pentasulphide. But the reactions did not occur and oxadiazin-6-ones were recovered or decomposed. Some of the oxadiazin-5-ones, oxadiazin-5-thiones and oxadiazin-6-ones have shown good antimicrobial activities.
In this study some new N-substituted pyridine carboxamide oximes are obtained from the reactions of pyridine hydroxamic acid chloride hydrochlorides with primary amines. The reactions of carboxamide oximes with chloroacetyl chloride in the presence of triethylamine gave the corresponding 3,4- disubstituted-1,2,4-oxadiazin-5-ones. 3,4-Disubstituted-1,2,4-oxadiazin -5- thiones are prepared in good yields by the reactions of 3,4-disubstituted-1,2,4- oxadiazin-5-ones and phosphorus pentasulphide. 3,5-Disubstituted-1,2,4-oxadiazin-6-ones are prepared by the reactions of a- amino acid ester hydrochlorides with pyridine hydroxamic acid chloride hydrochlorides. On the other hand, 2,5-disubstituted-1,3,4-oxadiazin-6-ones are obtained from the reactions of 2-oxoalkanoic acid acylhydrazones and DCC. We have previously shown that 3,4-disubstituted A2-1,2,4-oxadiazolin-5-thiones rearranged to the corresponding 3,4-disubstituted A2-1,2,4-thiadiazolin-5-ones. For the similar rearrangement we have attempted to prepare oxadiazin-6- thiones from the oxadiazin-6-ones, using phosphorus pentasulphide. But the reactions did not occur and oxadiazin-6-ones were recovered or decomposed. Some of the oxadiazin-5-ones, oxadiazin-5-thiones and oxadiazin-6-ones have shown good antimicrobial activities.
Description
Keywords
Amidoksimler, Oksadiazin, Amidoximes, Oxadiazin
Citation
Arıkan, N. (1998). Çeşitli oksadiazin-5-on, oksadiazin-6-on ve ilgili bileşiklerin sentezi. Yayınlanmamış doktora tezi. Uludağ Üniversitesi Fen Bilimleri Enstitüsü.