4.8 Article

TBAI/K2S2O8-Promoted [4+2] Annulation of Ketene N,S-Acetals and N-Tosylhydrazones toward Pyridazines

Journal

ORGANIC LETTERS
Volume 23, Issue 5, Pages 1606-1610

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00026

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Funding

  1. National Natural Science Foundation of China [22001140]
  2. Natural Science Foundation of Shandong Province, China [ZR2020QB002]
  3. Foundation of State Key Laboratory of Biobased Material and Green Papermaking, Qilu University of Technology, Shandong Academy of Sciences [ZZ20190111]

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A TBAI/K2S2O8-promoted [4 + 2] annulation of ketene N,S-acetals, and N-tosylhydrazones was efficiently developed, enabling straightforward access to a variety of trisubstituted pyridazines in reasonable to good yields. The synthetic methodology features a broad substrate scope and a good functional group tolerance. Control experiments demonstrated the indispensability of the alkylthio functionality in the enaminone substrates.
A TBAI/K2S2O8-promoted [4 + 2] annulation of ketene N,S-acetals, and N-tosylhydrazones was efficiently developed, enabling straightforward access to a variety of trisubstituted pyridazines in reasonable to good yields. The synthetic methodology features a broad substrate scope and a good functional group tolerance. Control experiments demonstrated the indispensability of the alkylthio functionality in the enaminone substrates.

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