Direct Access to Fused Salicylaldehydes and Salicylketones from Tetraynes

DOI Web Site Web Site 被引用文献2件
  • Yimin Hu
    Laboratory of Functional Molecular Solids, Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University, Wuhu Anhui 241000 P. R. China
  • Yadong Hu
    Laboratory of Functional Molecular Solids, Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University, Wuhu Anhui 241000 P. R. China
  • Qiong Hu
    Laboratory of Functional Molecular Solids, Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University, Wuhu Anhui 241000 P. R. China
  • Jie Ma
    Laboratory of Functional Molecular Solids, Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University, Wuhu Anhui 241000 P. R. China
  • Shuang Lv
    Laboratory of Functional Molecular Solids, Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University, Wuhu Anhui 241000 P. R. China
  • Baohua Liu
    Laboratory of Functional Molecular Solids, Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University, Wuhu Anhui 241000 P. R. China
  • Shaowu Wang
    Laboratory of Functional Molecular Solids, Ministry of Education Anhui Key Laboratory of Functional Molecular-Based Materials, Institute of Organic Chemistry School of Chemistry and Materials Science Anhui Normal University, Wuhu Anhui 241000 P. R. China

書誌事項

公開日
2017-02-06
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/chem.201605785
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>A facile method for the synthesis of fused, multifunctionalized salicylaldehydes and salicylketones by a one‐pot, three‐step cascade hexadehydro‐Diels–Alder (HDDA) reaction of tetraynes followed by an intermolecular aldehyde/ketone reaction and hydroxylation is reported. Target compounds were prepared by the condensation of malonates with 3‐bromo‐1‐propyne, and the resulting 2,2‐di(1‐propyn‐3‐yl)malonates underwent cross‐coupling with phenylethynyl bromides to afford 2,2‐di(5‐phenyl‐2,4‐pentadiynyl)malonates, which underwent intramolecular cyclization to produce bicyclic salicylaldehydes. The overall transformation involves the formation of four new C−C bonds and one new C<jats:sub>aryl</jats:sub>−O bond through both intramolecular and intermolecular reactions. The reaction is easy to perform, proceeds under mild conditions, and exhibits excellent regioselectivity. Water, a simple and readily available reagent, was employed as the OH source. A plausible reaction mechanism is proposed for this new annulation based on isotopic substitution experiments.</jats:p>

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