Transition-metal-free intramolecular Friedel-Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives


YILDIZ T., Bastas I., BAŞPINAR KÜÇÜK H.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, cilt.17, ss.2203-2208, 2021 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 17
  • Basım Tarihi: 2021
  • Doi Numarası: 10.3762/bjoc.17.142
  • Dergi Adı: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, Chemical Abstracts Core, Directory of Open Access Journals
  • Sayfa Sayıları: ss.2203-2208
  • Anahtar Kelimeler: alkene activation, intramolecular Friedel-Crafts alkylation, trifluoroacetic acid, xanthene, ONE-POT SYNTHESIS, ORTHO-QUINONE METHIDES, EFFICIENT SYNTHESIS, UNACTIVATED ALKENES, HYDROARYLATION, CYCLIZATION, XANTHONES, ARYNES, THIOXANTHONES, BUTOXIDE
  • İstanbul Üniversitesi Adresli: Hayır

Özet

In this work, new derivatives (substituted 9-methyl-9-arylxanthenes) of xanthene compounds (5a-l) of possible biological significance were synthesized by developing a new synthesis method. In order to obtain xanthene derivatives, the original alkene compounds to be used as the starting materials were synthesized in four steps using appropriate reactions. A cyclization reaction by intramolecular Friedel-Crafts alkylation was carried out in order to synthesize the desired xanthene derivatives using the alkenes as starting compounds. The intramolecular Friedel-Crafts reaction was catalyzed by trifluoroacetic acid (TFA) and provided some novel substituted 9-methyl-9-arylxanthenes with good yields at room temperature within 6-24 hours. As a result, an alkene compound was used for activation with TFA in the synthesis of xanthene through intramolecular Friedel-Crafts alkylation for the first time.