4.7 Article

Construction of 6H-benzo[c]thiochromenes via a tandem reaction of arynes with thionoesters

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 24, Pages 6979-6984

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo01177d

Keywords

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Funding

  1. National Natural Science Foundation of China [22161039]
  2. Excellent Young Teachers Plan of Bingtuan [2017CB001, CZ027203, CZ002203]
  3. International Cooperation Project of Shihezi University [GJHZ201801]

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A mild and transition-metal free tandem reaction has been developed for the construction of 6H-benzo[c]thiochromenes. Thionoesters react with arynes to afford different structures of products in yields ranging from 37-80% and 51-75%.
A mild and transition-metal free tandem reaction for the construction of 6H-benzo[c]thiochromenes has been developed. Thionoesters react with two molecules of arynes through a Diels-Alder cycloaddition/nucleophilic arylation process to afford 6-alkoxy-6-aryl-6H-benzo[c]thiochromenes in 37-80% yields. In addition, the Diels-Alder cycloaddition/aromatization tandem reaction of thionoesters with one molecule of aryne provides the construction of 6-alkoxyl-6H-benzo[c]thiochromenes in 51-75% yields.

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