CAS 1614240-02-6, Cat. No EN300-6427857
Reagent for heterocyclization
tert-Butyl N-(2-oxobut-3-yn-1-yl)carbamate is an enaminone precursor used in the synthesis of pyridine derivatives and reagent for СuAAC synthesis of pyrazoles1–3. It serves as an electron-poor alkyne, undergoing [3+2] cycloadditions with azomethine imines, leading to the formation of fluorescent pyrazole derivatives. Additionally, in pyridine synthesis, it participates in a [2+2] cycloaddition with enaminones derived from N-Boc protected amino acids, forming highly functionalized pyridine derivatives. The reagent is particularly useful for synthesizing 2-alkylamino-substituted pyridine-3,4-dicarboxylates, expanding its role in pharmaceutical research. It is moisture-sensitive and should be stored under an inert atmosphere.
Synonyms: (Z)-N-boc-2-acetylamino-3-butyn-2-yl acetate; tert-butyl N-(2-oxobut-3-yn-1-yl)carbamate; 1,1-dimethylethyl N-(2-oxo-3-butyn-1-yl)carbamate; carbamic acid, N-(2-oxo-3-butyn-1-yl)-, 1,1-dimethylethyl ester
Selected publications
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“Click” Chemistry: Application of Copper Metal in Cu-Catalyzed Azomethine Imine–Alkyne Cycloadditions.
Pušavec Kirar E.; Grošelj U.; Mirri G.; Požgan F.; Strle G.; Štefane B.; Jovanovski V.; Svete J. J Org Chem 2016, 81 (14), 5988–5997. DOI: 10.1021/acs.joc.6b00945
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Synthesis of Pyridines with an Amino Acid Residue by [2+2] Cycloadditions of Electron-Poor Acetylenes on Enaminone Systems Derived from N-Boc Protected Amino Acids.
Prek B.; Bezenšek J.; Stanovnik B. Tetrahedron 2017, 73 (35), 5260–5267. DOI: 10.1016/j.tet.2017.07.019
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Synthesis of Functionalized Pyrazole Derivatives by Regioselective [3+2] Cycloadditions of N-Boc-α-Amino Acid-Derived Ynones.
Kirar E. P.; Grošelj U.; Golobič A.; Poagan F.; Ričko S.; Štefane B.; Svete J. Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences 2018, 73 (7), 467–480. DOI: 10.1515/znb-2018-0013