Synonyms:tetrahydropyrazine;1,2,3,4-tetrahydropyrazine;5194-05-8;DTXSID70551130;AKOS006357478
95% *data from raw suppliers
The study presents a novel method for synthesizing unsaturated heterocyclic compounds, specifically protected tetrahydropyrazines and related heterocycles, through a copper-catalyzed double amination of haloacetylenes. The researchers discovered that while attempting N,N'-dialkynylation of a diamine derivative, they unexpectedly obtained tetrahydropyrazine derivatives instead of the expected dialkynylated product. The proposed reaction mechanism involves an initial alkynylation of a sulfonamide with a haloacetylene, followed by a second amination in a 6-endo-dig manner under copper catalysis. The study demonstrates the generality of this method using both aliphatic and aromatic acetylenes, and it also highlights the versatility of the protocol by showing its applicability to the synthesis of broader types of heterocycles, including seven-membered heterocycles and N,O-heterocycles. The role of the sulfonylamino group in facilitating the endo-type ring closure is emphasized, and the study concludes that this simple one-step method is suitable for the direct preparation of protected surrogates of unstable tetrahydropyrazines.
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