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Preparation and Utility of N-Alkynyl Azoles in Synthesis

Department of Chemistry, University of Texas at Austin, Austin, TX 78712, USA
Department of Chemistry & Biochemistry, Texas State University, San Marcos, TX 78666, USA
Author to whom correspondence should be addressed.
Molecules 2019, 24(3), 422;
Received: 21 December 2018 / Revised: 16 January 2019 / Accepted: 22 January 2019 / Published: 24 January 2019
(This article belongs to the Special Issue Alkynes: From Reaction Design to Applications in Organic Synthesis)
Heteroatom-substituted alkynes have attracted a significant amount of interest in the synthetic community due to the polarized nature of these alkynes and their utility in a wide range of reactions. One specific class of heteroatom-substituted alkynes combines this utility with the presence of an azole moiety. These N-alkynyl azoles have been known for nearly 50 years, but recently there has been a tremendous increase in the number of reports detailing the synthesis and utility of this class of compound. While much of the chemistry of N-alkynyl azoles mirrors that of the more extensively studied N-alkynyl amides (ynamides), there are notable exceptions. In addition, as azoles are extremely common in natural products and pharmaceuticals, these N-alkynyl azoles have high potential for accessing biologically important compounds. In this review, the literature reports of N-alkynyl azole synthesis, reactions, and uses have been assembled. Collectively, these reports demonstrate the growth in this area and the promise of exploiting N-alkynyl azoles in synthesis. View Full-Text
Keywords: alkynes; cyclizations; natural products; carbenes; polymers alkynes; cyclizations; natural products; carbenes; polymers
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MDPI and ACS Style

Reinus, B.; Kerwin, S.M. Preparation and Utility of N-Alkynyl Azoles in Synthesis. Molecules 2019, 24, 422.

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