Preparation and Utility of N-Alkynyl Azoles in Synthesis

Abstract

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.

CuI/DMAP‐Catalyzed Oxidative Alkynylation of 7‐Azaindoles: Synthetic Scope and Mechanistic Studies

“…For CuF 2 /DMAP catalyzed N ‐vinylation of 7‐azaindoles, we have isolated an active [Cu II (DMAP) 4 Cl 2 ] complex and described the dual role of DMAP as a base as well as a ligand to the formation of N ‐vinyl derivatives (Scheme 1b) [21b] . In both cases, we proposed a plausible mechanism based on our findings [7b] . Thus, keeping our interest high on the derivatization of the 7‐azaindole system, [22,23] herein, we report the CuI/DMAP‐catalyzed oxidative N ‐alkynylation of 7‐azaindoles (Scheme 1c) at room temperature and ambient atmosphere.…”

Introductory Chapter: Azoles, Their Importance, and Applications

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versatile and useful compounds with potential applications in various areas such as materials, energetics, catalysis, etc. The intensive research work in the area of azoles, covering synthesis, characterization, and computational studies of their various novel derivatives is continuously ongoing [44,[47][48][49][50][51][52]. Thus, the area of azoles and their derivatives, their physico-chemical properties, and applications is of continuous high interest, and therefore this book will be a valuable addition to the knowledge which has been accumulated so far in this field.

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