4.8 Article

Synthesis of Highly Functionalized Pyridines: A Metal-Free Cascade Process

Journal

ORGANIC LETTERS
Volume 23, Issue 17, Pages 6669-6673

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02234

Keywords

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Funding

  1. National Natural Science Foundation of China [U1702286, 21572197, 21762047, 21901224]
  2. Program for Changjiang Scholars and Innovative Research Team in University [IRT17R94]
  3. Ling-Jun Scholars of Yunnan Province [202005AB160003]
  4. Talent Plan of Yunnan Province [YNWR-QNBJ-2018-025]

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A new synthesis process for highly functionalized pyridines has been reported, utilizing a tandem reaction sequence. This method provides good yields of pyridines with accessible starting materials and shows potential for modifying frameworks of BINOL and natural products.
Herein, we report a new process for the synthesis of highly functionalized pyridines based on a tandem Pummerer-type rearrangement, aza-Prins cyclization, and elimination-induced aromatization. This formal [5+1] cyclization provides pyridines in good yields with easily accessible starting materials. The synthetic potential of our new method is further demonstrated in the modification of the frameworks of BINOL and some natural products.

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