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Bsi(OTf)3-mediated tandem annulation of 1-aryl isochroman-3-ones with oxygenated arenes: one-pot synthesis of polyoxygenated homotriptycenes.
Chang, Meng-Yang; Lin, Chun-Yi; Chen, Shin-Mei; Hsiao, Yu-Ting.
Affiliation
  • Chang MY; Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan. mychang@kmu.edu.tw and Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan.
  • Lin CY; Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan. mychang@kmu.edu.tw.
  • Chen SM; Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan. mychang@kmu.edu.tw.
  • Hsiao YT; Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan. mychang@kmu.edu.tw.
Org Biomol Chem ; 19(21): 4733-4742, 2021 06 02.
Article in En | MEDLINE | ID: mdl-33970174
Bi(OTf)3 (bismuth triflate)-mediated one-pot tandem annulation of oxygenated 1-aryl isochroman-3-ones with oxygenated arenes provides polyoxygenated homotriptycenes in moderate to good yields in MeNO2 at reflux (101 °C) for 10 h under an air atmosphere and easy-operational conditions via intermolecular and intramolecular Friedel-Crafts type procedures. A plausible mechanism is proposed and discussed. This protocol provides a highly effective ring-closure via three carbon-carbon (C-C) bond formations.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2021 Type: Article Affiliation country: Taiwan
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2021 Type: Article Affiliation country: Taiwan