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Ytterbium-Catalyzed Tandem Diels–Alder/aza-Claisen Rear-rangement/Decarboxylation of N-Allenamides for the Synthesis of Diarylmethanes
  • +3
  • Bin Chen,
  • Shan Zhong,
  • Huilin Zhan,
  • Zhengyu Han,
  • Jianwei Sun,
  • Hai Huang
Bin Chen
Changzhou University
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Shan Zhong
Changzhou University
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Huilin Zhan
Changzhou University
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Zhengyu Han
Changzhou University
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Jianwei Sun
The Hong Kong University of Science and Technology
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Hai Huang
Changzhou University

Corresponding Author:huanghai@cczu.edu.cn

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Abstract

not-yet-known not-yet-known not-yet-known unknown A tandem Diels–Alder reaction / aza-Claisen rearrangement / decarboxylation strategy of N-allenamides with 3-alkoxycarbonyl-2-pyrones has been developed for the efficient synthesis of diarylmethanes with moderate to good yields. The reac-tion exhibits good functional group tolerance and can be applied to late-stage modifications of known drug molecules. Mechanistic studies indicate that the ester group at the 3-position of 2-pyrones is essential, and the initial Diels–Alder reaction between the 2-pyrones with the proximal C=C bond of the N-allenamides is crucial for the success of the reaction.
14 Aug 2024Submitted to Chinese Journal of Chemistry
20 Aug 2024Submission Checks Completed
20 Aug 2024Assigned to Editor
20 Aug 2024Review(s) Completed, Editorial Evaluation Pending
23 Aug 2024Reviewer(s) Assigned
19 Sep 2024Editorial Decision: Revise Minor
28 Sep 20241st Revision Received
29 Sep 2024Submission Checks Completed
29 Sep 2024Assigned to Editor
29 Sep 2024Review(s) Completed, Editorial Evaluation Pending
29 Sep 2024Editorial Decision: Accept