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PYRAZINE- AND PYRIDINE-SUBSTITUTED PROP-2-YN-1-OLS, BUT-3-YN-2-OLS, AND BUT-3-YN-2-ONES – PURIFICATION, STABILITY, AND HANDLING REVISED

Claudia Schindler, Carola Schulzke
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Abstract


A short series of alkynyl-substituted pyrazine and pyridine compounds were synthesized by palladium catalysed Sonogashira cross-coupling reactions between aryl halides and alkynes. All products are either white solids or colorless liquids, which is partly in contrast to previous reports. After purification a color change or intense darkening was observed; in some cases starting almost immediately. Both, the nature of the heteroaromatic ring and the substituents of the alkyne moiety affect their stability. Herein details of synthesis, characterization and, most importantly, purification and handling are reported. Furthering the understanding of the compounds’ properties should facilitate exploiting theirs and their derivatives’ huge synthetic potential in the future. The reactive alkynyl-substituted pyrazine and pyridine compounds might then play an even more important role as precursors for pharmaceutical compounds and in the in vitro synthesis of natural products.

How to Cite
Schindler, C.; Schulzke, C. Chem. Heterocycl. Compd. 2015, 51, 1008. [Khim. Geterotsikl. Soedin. 2015, 51, 1008.]

For this article in the English edition see DOI 10.1007/s10593-016-1811-0


Keywords


alkynylpyrazines; alkynylpyridines; alcohol oxidation; purification; Sonogashira cross-coupling reaction; stability

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