Preparation and Utility of N-Alkynyl Azoles in Synthesis




Reinus, Brandon
Kerwin, Sean M.

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Multidisciplinary Digital Publishing Institute


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.



carbenes, cyclizations, natural products, polymers, alkynes, Chemistry and Biochemistry


Reinus, B., & Kerwin, S. M. (2019). Preparation and Utility of N-Alkynyl Azoles in Synthesis. Molecules, 24(3): 422.


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