Synthetic studies pertaining to the 2,3-pyridyne and 4,5-pyrimidyne

We report synthetic studies pertaining to two heterocyclic aryne intermediates: the 2,3-pyridyne and the 4,5-pyrimidyne. First, a 2,3-pyridyne precursor was readily accessed from 2-pyridone using a known procedure. Subsequently, 2,3-pyridyne generation and trapping were used to access several functi...

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Bibliographic Details
Published in:Tetrahedron 2016-06, Vol.72 (26), p.3629-3634
Main Authors: Medina, Jose M., Jackl, Moritz K., Susick, Robert B., Garg, Neil K.
Format: Article
Language:English
Subjects:
Hetarynes
Heterocycles
Precursors
Pyridine
Pyridines
Pyridyne
Pyrimidyne
Synthesis
Tetrahedrons
Trapping
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Summary:We report synthetic studies pertaining to two heterocyclic aryne intermediates: the 2,3-pyridyne and the 4,5-pyrimidyne. First, a 2,3-pyridyne precursor was readily accessed from 2-pyridone using a known procedure. Subsequently, 2,3-pyridyne generation and trapping were used to access several functionalized pyridines in a regioselective manner. In addition, we report synthetic routes to two isomeric silyltriflates, which were intended to serve as precursors to the 4,5-pyrimidyne. Consecutive 4,5-pyrimidyne generation and trapping experiments were ultimately deemed unfruitful. We expect these findings will promote the use of 2,3-pyridyne and other heterocyclic arynes as building blocks for the synthesis of functionalized heterocycles. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2016.02.038