4,6-Dimetoksibenzofuran-7-Karbaldehitlerin Dakin Oksidasyonu: Benzofuran-7-ol Bileşiklerinin Sentezi

Yıl 2025, Cilt: 25 Sayı: 6, 1308 - 1315

Hakan Kandemir , Tuğçe Nur Uslu Uçar , İbrahim Fazıl Şengül

Öz

Dakin oksidasyonu ile 4,6-dimetoksibenzofuran-7-karbaldehitlerin 6-metoksi-benzofuran-4,7-kinonlara dönüşümü daha önce tarafımızdan rapor edilmiştir. Bu çalışmada ise, Dakin oksidasyon reaksiyonunda kullanılan hidrojen peroksit (H₂O₂) miktarının reaksiyon üzerindeki etkisi araştırılmıştır. Reaksiyon koşullarının optimize edilmesiyle, başarılı bir şekilde benzofuran-7-ol türevleri elde edilmiştir. Elde edilen sonuçlar, H₂O₂ miktarının ürün seçiciliği üzerindeki etkisini ortaya koymakta ve benzofuran türevlerinin verimli sentez stratejilerinin geliştirilmesine katkı sağlamaktadır. Sentezlenen 4,6-dimetoksibenzofuran-7-ol yapıların karakterizasyonu, ¹H NMR, ¹³C NMR, FT-IR ve kütle spektrum analizleri kullanılarak gerçekleştirilmiştir. Ayrıca, uygun kristal yapıya sahip bileşiklerin yapıları X-ışını kırınım analizi ile de doğrulanmıştır.

Anahtar Kelimeler

Heterosiklik , Dakin oksidasyon , Benzofuran

Proje Numarası

122Z598

Dakin Oxidation of 4,6-Dimethoxybenzofuran-7-Carbaldehydes: Synthesis of Benzofuran-7-ols

Öz

The conversion of 4,6-dimethoxybenzofuran-7-carbaldehydes to the 6-methoxy-benzofuran-4,7-quinones by the Dakin oxidation was reported by us. In the current work, we explored the effect of varying amount of hydrogen peroxide (H₂O₂) on the outcome of the Dakin oxidation reaction. By optimizing the reaction conditions, benzofuran-7-ol derivatives were successfully prepared. The results provide insight into the influence of H₂O₂ quantity on product selectivity, contributing to the development of efficient synthetic strategies for benzofuran derivatives. The structures of the synthesized 4,6-dimethoxy-benzofuran-7-ols were confirmed employing ¹H NMR, ¹³C NMR, FT-IR and mass spectral analyses. Additionally, the structures of compounds with suitable crystalline forms were further confirmed by X-ray diffraction analysis.

Anahtar Kelimeler

Heterocyclic , Dakin Oxidation , Benzofuran

Destekleyen Kurum

TUBİTAK

Proje Numarası

122Z598

Teşekkür

This study was supported by Scientific and Technological Research Council of Turkey (TUBITAK) under the Grant Number 122Z598. The authors thank TUBITAK for their support.

Kaynakça

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