4-(Hetarilazoil)anilinlerin Skuaramik Asit Türevlerinin Sentezi ve Karakterizasyonu

Year 2020, Volume: 10 Issue: 1, 386 - 398, 01.03.2020

Fatih Eyduran Mine Aydoğan Yerlikaya

https://doi.org/10.21597/jist.542445

Abstract

Çalışmada, azo grubu taşıyan skuaramik asitlerin (bileşikler 4-6) sentezleri tek-kap içerisinde gerçekleştirildi. Bileşikler 4-6’nın sentezi için önce serbest amino grubu içeren azo boyarmaddeleri (bileşikler 1-3), diazo-kenetlenme yöntemiyle elde edildi. Bu yöntemde, çıkış bileşiği 3-hidroksi-4-metoksi-siklobut-3-en-1,2-dion, metanol ortamında, metanolün skuarik asit ile tekli yerdeğiştirmesi sonucunda elde edilmiş ve izole edilmeden bileşikler 4-6’nın sentezinde kullanılmıştır. Bileşikler 4-6, elde edilen bileşikler 1-3’ün 3-hidroksi-4-metoksi-siklobut-3-en-1,2-dion arasındaki tekli yerdeğiştirme tepkimesi sonucunda tek-kap içerisinde metanol ortamında düşük verimlerle sentezlenmiştir. Bileşikler 2, 4, 5 ve 6’nın kimyasal yapıları, spektroskopik yöntemler (FTIR, NMR) ile aydınlatılmıştır. Ayrıca, farklı çözelti ortamlarında bileşikler 4-6’nın UV-Görünür bölge absorpsiyon spektrumları alınmış ve değerlendirilmiştir. Bu sentez yönteminde, bileşikler 1-3, 3-hidroksi-4-metoksi-siklobut-3-en-1,2-dion’un -OCH3 grubu ile -OH grubuna göre bişelik 3 hariç seçimli yer değiştirdiği belirlenmiştir.

Keywords

Azo, Skuarik asit, Spektroskopi, Skuaramik asit

Synthesis and Characterization of Squaramic Acid Derivatives of 4-(Hetarilazoil)anilines

Abstract

In the study, synthesis of squaramic acids having azo group (compounds 4-6) were carried out in a one-pot. For the synthesis of compounds 4-6, firstly azo dyes bearing the free amine group (compounds 1-3) were obtained by the diazo-coupling method. In this method, the starting compound 3-hydroxy-4-methoxy-cyclobut-3-en-1,2-dione was obtained in the methanol medium as a result of the single substitution of methanol with squaric acid and used in the synthesis of compounds 4-6 without isolation. Compounds 4-6 were synthesized in a one-pot in a low yield in methanol medium as a result of single displacement reaction between compounds 1-3 and 3-hydroxy-4-methoxy-cyclobut-3-en-1,2-dione. Chemical structures of compounds 2, 4, 5, 6 were confirmed by spectroscopic methods (FTIR, NMR). In addition, UV-Vis absorption spectra of compounds 4-6 in different solutions were taken and evaluated. In this synthesis method, it was determined that compound 1 and 2 were selectively substituted with the -OCH3 group of 3-hydroxy-4-methoxy-cyclobut-3-en-1,2-dione compared -OH group.

Keywords

Azo, Squaric acid, Spectroscopy, Squaramic acid

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