Journal
TETRAHEDRON
Volume 72, Issue 26, Pages 3629-3634Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.02.038
Keywords
Heterocycles; Hetarynes; Pyridine; Pyridyne; Pyrimidyne
Categories
Funding
- NIH-NIGMS [R01 GM090007]
- A. P. Sloan Foundation
- Dreyfus Foundation
- University of California, Los Angeles
- UCLA Cota Robles Fellowship Program
- UCLA Gold Shield Alumnae
- Oskar-Jeger Scholarship Program
- NSF [CHE-1048804]
- NIH NCRR [S10RR025631]
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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 silyltrifiates, 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. (C) 2016 Elsevier Ltd. All rights reserved.
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