Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones
Yazarlar (4)
Doç. Dr. Kıymet BERKİL AKAR Tokat Gaziosmanpaşa Üniversitesi, Türkiye
Osman Çakmak İstanbul Rumeli Üniversitesi, Türkiye
Orhan Büyükgüngör
Ondokuz Mayıs Üniversitesi, Türkiye
Ondokuz Mayıs Üniversitesi, Türkiye
Ertan Şahin Atatürk Üniversitesi, Türkiye
| Makale Türü | Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale) | ||
| Dergi Adı | BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (Q4) | ||
| Dergi ISSN | 1860-5397 Wos Dergi Scopus Dergi | ||
| Dergi Tarandığı Indeksler | SCI-Expanded | ||
| Makale Dili | İngilizce | Basım Tarihi | 07-2011 |
| Cilt / Sayı / Sayfa | 7 / 7 / 1036–1045 | DOI | 10.3762/bjoc.7.118 |
| Makale Linki | http://dx.doi.org/10.3762/bjoc.7.118 | ||
| Özet |
| Efficient and stereoselective syntheses are described for the preparation of 2, 3, 9, 10-tetrabromo-1, 4-dimethoxy-1, 2, 3, 4-tetrahydroanthracenes 7, 8 and the corresponding 1, 4-diol 17 by silver ion-assisted solvolysis of hexabromotetrahydroanthracene 6. Base-promoted aromatization of 7 and 8 afforded synthetically valuable tribromo-1-methoxyanthracenes 10 and 11. The reaction of 17 with sodium methoxide generated tribromodihydroanthracene-1, 4-diol 27, whose oxidation with PCC gave 2, 9, 10-tribromoanthracene-1, 4-dione (28). Therefore a selective and efficient method was developed for the preparation of compound 28 starting from 9, 10-dibromoanthracene (1), in a simple four-step process. Compounds 10 and 11, and diol 27 constitute key precursors for the preparation of functionalized substituted anthracene derivatives that are difficult to prepare by other routes. The studies also reveal the broad range of reactivity and selectivity of the stereoisomeric anthracene derivatives. |
| Anahtar Kelimeler |
| anthracene derivatives | anthracene-1,4-dione | aromatization | bromination | bromoanthracene | methoxyanthracene | silver-induced substitution |
BM Sürdürülebilir Kalkınma Amaçları
| Atıf Sayıları | |
| Google Scholar | 8 |
| Web of Science | 6 |