4-((3-(Triflorometil)piridin-2-il)oksi)benzohidrazit Birimi İçeren Yeni Hidrazon Türevlerinin Sentezi

Year 2021, Volume: 11 Issue: 4, 2870 - 2879, 15.12.2021

Aytekin Köse

https://doi.org/10.21597/jist.902184

Abstract

Bu çalışmada, 4-((3-(triflorometil)piridin-2-il)oksi)benzohidrazit birimi bulunduran yedi yeni hidrazon türevlerinin sentezi gerçekleştirildi. Başlangıç bileşiği olarak kullanılan 4-hidroksibenzoik asit metanol içerisinde katalitik miktarda sülfürik asit ile metil esterine dönüştürüldü. Ester bileşiği, 2-bromo-3(triflorometil)piridin ile reaksiyona sokularak 4-((3-(triflorometil)piridin-2-il)oksi)benzoikasit metil esteri elde edildi. Daha sonra Ester bileşiği hidrazin hidrat ile hidrazitine dönüştürüldü. Hidrazit bileşiği seçilmiş sübstitüe aldehitler ile katılma-eliminasyon reaksiyonuna maruz bırakılarak hedef hidrazon türevleri sentezlendi. Sentezlenen bileşiklerin yapıları 1H, 13C NMR ve HRMS spektroskopileri ile aydınlatıldı. Toplamda dört kademe organik sentez, basit kimyasal modifikasyonlar, yüksek skalada sentezlenebilme, ucuz kimyasal reaktifler ve kısa sentez süreleri bu çalışmanın avantajları olarak belirlendi.

Keywords

Hidrazit, metilparaben, SNAr mekanizması, hidrazon, 2-bromo-3(triflorometil)piridin, kondenzasyon reaksiyonu

Synthesis of New Hydrazone Derivatives Bearing 4-((3-(trifluoromethyl)pyridin-2- yl)oxy)benzohydrazide

Abstract

In this work, seven new hydrazone derivatives containing 4-((3-(trifluoromethyl)pyridin-2-yl)oxy) benzohydrazide unit were synthesized. The 4-hydroxybenzoic acid used as the starting compound was converted to its methyl ester with a catalytic amount of sulfuric acid in methanol. The ester compound was reacted with 2-bromo-3-(trifluoromethyl)pyridine to give 4-((3-(trifluoromethyl)pyridin-2-yl)oxy)benzoic acid methyl ester. The ester compound was then converted to hydrazide with hydrazine hydrate. Target hydrazone derivatives were synthesized by reacting the hydrazide compound with selected substituted aldehydes via an addition-elimination reaction. The structures of the synthesized compounds were elucidated by 1H, 13C NMR and HRMS spectroscopies. In total, four steps of organic synthesis, simple chemical modifications, high-scaled synthesizing, cheap chemical reagents and short synthesis times were determined as the advantages of this study.

Keywords

Hydrazide, methylparaben, SNAr mechanism, hydrazone, 2-bromo-3-(trifluoromethyl)pyridine, condensation reaction

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