Microwave assisted synthesis of some new Schiff’s bases from 2,4-dihydro-3H-1,2,4-triazol-3-one

Yıl 2021, , 1 - 5, 29.06.2021

Emre Menteşe , Fatih Yılmaz , Bahittin Kahveci

https://doi.org/10.53501/rteufemud.819653

Öz

In this manuscript, a new series of 1,2,4-triazole-3-ones containing imin function was synthesized from 5-(4-bromobenzyl)-4-amino-2H-1,2,4-triazol-3(4H)-one and aromatic aldehyde by using microwave irradiation technique via schiff base reaction. Firstly, ethyl imido-p-bromophenylacetate hydrochloride (2) was synthesized according to the pinner method in the literature. Then, compound 2 was reacted with ethyl carbazate to synthesized ethyl p-bromophenylacetate etoxycarbonylhydrazone (3) compound. Then, 5-(4-bromobenzyl)-4- amino-2H-1,2,4-triazol-3(4H)-one (4) was synthesized from the reaction of ethyl p-bromophenylacetate etoxycarbonylhydrazone (3) with hydrazine monohydrate. Then, it was converted to their corresponding triazole containing Schiff bases (5a-e) with the reaction of corresponding aromatic aldehydes in ethanol by using the microwave irradiation method. This microwave technique has some advantages, including rapid and uniform heating, higher product yield and purity, mild reaction conditions, low energy requirement and shorter reaction time. The chemical structures of newly synthesized triazole containing schiff bases were identified using IR, 1HNMR, and mass spectroscopy data.

Anahtar Kelimeler

Triazole, Schiff base, Microwave synthesis, Hydrazine monohydrate

Bazı Schiff bazlarının 2,4-dihidro-3H-1,2,4-triazol-3-on'dan mikrodalga destekli sentezi

Öz

Bu çalışmada, imin grubu içeren yeni bir seri 1,2,4-triazol-3-on türevleri mikrodalga destekli sentezlenmiştir. 5- ( 4 -Bromobenzil) - 4 - amino- 2H - 1,2,4 - triazol - 3(4H) - on bileşiği ester etoksikarbonil hidrazonun hidrazin hidrat ile reaksiyonundan elde edilmiş ve daha sonra bu bileşik çeşitli aldehitler kullanılarak Schiff bazlarına dönüştürülmüştür. Yeni sentezlenen bileşiklerin yapı aydınlatılmasında IR, 1H-NMR ve kütle spektroskopisi kullanıldı.

Bu çalışmada, imin grubu içeren yeni bir seri 1,2,4-triazol-3-on türevleri mikrodalga destekli sentezlenmiştir. 5- ( 4 -Bromobenzil) - 4 - amino- 2H - 1,2,4 - triazol - 3(4H) - on bileşiği ester etoksikarbonil hidrazonun hidrazin hidrat ile reaksiyonundan elde edilmiş ve daha sonra bu bileşik çeşitli aldehitler kullanılarak Schiff bazlarına dönüştürülmüştür. Yeni sentezlenen bileşiklerin yapı aydınlatılmasında IR, 1H-NMR ve kütle spektroskopisi kullanıldı.

Anahtar Kelimeler

triazol, Schiff bazı, mikrodalga sentez, hidrazon

Kaynakça

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