Keywords
Acetylene
calcium carbide
lactams
synthetic peptides.
vinyl carboxamides
vinylation
Abstract
Direct N-vinylation of lactams with calcium carbide water system was performed under super-basic conditions. The vinylation occurred exclusively at NH group leaving C=O function intact to afford cyclic N-vinyl amides in yields up to 97%. The obtained products are prospective monomers for the preparation of synthetic peptides.
References
.
Bidusenko I.A., Schmidt E.Y., Protsuk N.I., Ushakov I.A., Vashchenko A.V., Afonin A.V., Trofimov B.A.
Organic Letters,
2020
.
Cortez-Lemus N.A., Licea-Claverie A.
Progress in Polymer Science,
2016
.
Ma X., Wang Z., Liu Z., Li Z.
Chinese Journal of Chemistry,
2021
.
Generation, regeneration, and recovery of Cu catalytic system by changing the polarity of electrodes
Rodygin K.S., Samoylenko D.E., Seitkalieva M.M., Lotsman K.A., Metlyaeva S.A., Ananikov V.P.
Green Chemistry,
2022
.
Metlyaeva S.A., Rodygin K.S., Lotsman K.A., Samoylenko D.E., Ananikov V.P.
Green Chemistry,
2021
.
Lebedev A.N., Rodygin K.S., Mironenko R.M., Saybulina E.R., Ananikov V.P.
Journal of Catalysis,
2022
.
Werner G., Rodygin K.S., Kostin A.A., Gordeev E.G., Kashin A.S., Ananikov V.P.
Green Chemistry,
2017
.
An J., Ma X., Luo S., Weng C., Ding Y., Ling C., Szostak M.
Synlett,
2020
.
Teong S.P., Lim J., Zhang Y.
ChemSusChem,
2017
.
Oparina L.A., Khil’ko M.Y., Chernyshova N.A., Shaikhudinova S.I., Parshina L.N., Preiss T., Henkelmann J., Trofimov B.A.
Russian Journal of Organic Chemistry,
2005
.
Beletskaya I.P., Ananikov V.P.
Chemical Reviews,
2022
.
Bosch M., Schlaf M.
Journal of Organic Chemistry,
2003
.
Kubota M., Nainar S., Parker S.M., England W., Furche F., Spitale R.C.
ACS Chemical Biology,
2019
.
Sitte N.A., Menche M., Tužina P., Bienewald F., Schäfer A., Comba P., Rominger F., Hashmi A.S., Schaub T.
Journal of Organic Chemistry,
2021
.
Gupta M., Levine S.R., Spitale R.C.
Accounts of Chemical Research,
2022
.
Fan W., Yamago S.
Angewandte Chemie - International Edition,
2019
.
Vitkovskaya N.M., Orel V.B., Kobychev V.B., Bobkov A.S., Absalyamov D.Z., Trofimov B.A.
International Journal of Quantum Chemistry,
2020
.
Kawatani R., Kelland M.A., Ajiro H.
Journal of Applied Polymer Science,
2020
.
Spiegelberg B., Jiao H., Grauke R., Kubis C., Spannenberg A., Brandt A., Taden A., Beck H., Tin S., Vries J.G.
Advanced Synthesis and Catalysis,
2022
.
Panarin E.F.
Russian Chemical Bulletin,
2015
.
Semina E., Tuzina P., Bienewald F., Hashmi A.S., Schaub T.
Chemical Communications,
2020
.
Yang P., Liu X., Li X., Wei M.
Organic Chemistry Frontiers,
2021
.
Synthesis of 1,3- and 1,2,3-functionalized pyrroles via Ir(I)-catalyzed vinylation of allyl alcohols
Alavez-Rosas D., Maldonado-Domínguez M., González-Antonio O., Romero-Ávila M., Méndez-Stivalet J., Flores-Pérez B.
Chemistry of Heterocyclic Compounds,
2017
.
Trofimov B.A., Oparina L.A., Parshina L.N., Khil’ko M.Y., Tantsyrev A.P., Aleksandrova G.P.
Cellulose,
2013
.
Kawatani R., Hamawaki T., Waku T., Tanaka N., Ajiro H.
Macromolecular Chemistry and Physics,
2023
.
Gyrdymova Y.V., Samoylenko D.E., Rodygin K.S.
Chemistry - An Asian Journal,
2022
.
Mondal K., Patra S., Halder P., Mukhopadhyay N., Das P.
Organic Letters,
2022
.
Lotsman K.A., Rodygin K.S., Skvortsova I., Kutskaya A.M., Minyaev M.E., Ananikov V.P.
Organic Chemistry Frontiers,
2023
.
Colacino E., De Luca G., Liguori A., Napoli A., Siciliano C., Sindona G.
Nucleosides, Nucleotides and Nucleic Acids,
2003
.
Kurmaz S.V., Pyryaev A.N.
Mendeleev Communications,
2010
.
Lotsman K., Rodygin K.
Green Chemistry,
2023
.
.
Rodygin Konstantin S., Gyrdymova Yulia V., Ananikov Valentine P.
Russian Chemical Reviews,
2022
.
Liao H., Li Z.
Tetrahedron Letters,
2023
.
Semenova N.V., Schmidt E.Y., Ushakov I.A., Trofimov B.A.
Mendeleev Communications,
2023
.
Kurokhtina A.A., Larina E.V., Lagoda N.A., Schmidt A.F.
Mendeleev Communications,
2024