Get access

Synthesis of Pyridines by Carbenoid-Mediated Ring Opening of 2H-Azirines

Authors

  • Nicole S. Y. Loy,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
    Search for more papers by this author
  • Dr. Alok Singh,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
    Search for more papers by this author
  • Dr. Xianxiu Xu,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
    Search for more papers by this author
  • Prof. Cheol-Min Park

    Corresponding author
    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)
    • Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore)===

    Search for more papers by this author

  • We thank Dr. Rakesh Ganguly for X-ray crystallographic analysis. We acknowledge the Nanyang Technological University for financial support.

Abstract

original image

Roaming the range: The title reaction tolerates a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′-tetramethyl-1,3-benzenedipropionic acid). The formation of the key intermediate is catalyst-controlled, and subsequent cyclization and oxidation affords pyridines in excellent yields. The method has been used for the efficient synthesis of polyarylpyridines.

Get access to the full text of this article

Ancillary