Abstract:
New N-Boc-alkyl(2-alkynylcyclopropyl)amines were synthesized from 1-alkynyl-1-chlorocyclopropanes and N-Boc- alkylamines under the action of ButOK in DMSO, the intermediates having been the corresponding conjugated alkynylcyclopropenes. The Boc-derivatives can be converted into free secondary 2-alkynylcyclopropylamines, as well as β-lithiated with subsequent alkylation.
Citation:
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “Synthesis of vicinal (alkylamino)alkynylcyclopropanes from geminal alkynyl(chloro)cyclopropanes”, Mendeleev Commun., 31:5 (2021), 654–656
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https://www.mathnet.ru/eng/mendc1012
https://www.mathnet.ru/eng/mendc/v31/i5/p654
This publication is cited in the following 5 articles:
Philippe Bertus, Julien Caillé, “Advances in the Synthesis of Cyclopropylamines”, Chem. Rev., 2025
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, “Electrophilic functionalization of N-substituted vicinal alkynyl(amino)cyclopropanes via selective lithiation”, Russ Chem Bull, 72:8 (2023), 1781
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, “Regio- and stereoselective synthesis of functionalized N-Boc-2-alkynylcyclopropylamines”, Russ Chem Bull, 71:8 (2022), 1830
V. D. Gvozdev, K. N. Shavrin, M. P. Egorov, O. M. Nefedov, “Methods for the synthesis of functionalized alkynylcyclopropanes”, Russ Chem Bull, 70:11 (2021), 2051
Yu. V. Tomilov, L. G. Menchikov, E. A. Shapiro, V. D. Gvozdev, K. N. Shavrin, N. V. Volchkov, M. B. Lipkind, M. P. Egorov, S. E. Boganov, V. N. Khabashesku, E. G. Baskir, “Carbenes, related intermediates, and small-sized cycles: contribution from Professor Nefedov's laboratory”, Mendeleev Commun., 31:6 (2021), 750–768
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