Abstract
The first representatives of silicon-containing azocarboxamides, N,N′-bis(silylmethyl) azodicarboxamides, were synthesized by the reaction of diisopropyl azodicarboxylate with α-silylamines MeNHCH2SiMen(OMe)3–n (n = 0–2).
Similar content being viewed by others
REFERENCES
Zhu, C., Chen, P., Zhu, R., Lin, Z., Wu, W., and Jiang, H., Chem. Commun., 2017, vol. 53, no. 18, p. 267. https://doi.org/10.1039/c6cc10187a
Berna, J., Alajarı, M., and Orenes, R.-A., J. Am. Chem. Soc., 2010, vol. 132, no. 31, p. 10741. https://doi.org/10.1021/ja101151t
Bern, J., Alajarın, M., Marın-Rodrıguez, C., and Franco-Pujante, C., Chem. Sci., 2012, vol. 3, no. 7, p. 2314. https://doi.org/10.1039/c2sc20488f
Amirjalayer, S., Martinez-Cuezva, A., Bern, J., Woutersen, S., and Buma, W.J., Angew. Chem. Int. Ed., 2018, vol. 57, no. 7, p. 1792. https://doi.org/10.1002/anie.201709666
Sommer, M.G., Marinova, S., Krafft, M.J., Urankar, D., Schweinfurth, D., Bubrin, M., Košmrlj, J., and Sarkarm, B., Organometallics, 2016, vol. 35, no. 17, p. 2840. https://doi.org/10.1021/acs.organomet.6b00424
Klein, J., Beerhues, J., Schweinfurth, D., van der Meer, M., Gazvoda, M., Lahiri, G.K., Košmrlj, J., and Sarkar, B., Chem. Eur. J., 2018, vol. 24, no. 68, p. 18020. https://doi.org/10.1002/chem.201803606
Urankar, D., Pevec, A., and Košmrlj, J., Eur. J. Inorg. Chem., 2011, no. 12, p. 1921. https://doi.org/10.1002/ejic.201001051
Ksošmrlj, M., Kočevar, M., and Polanc, S., Synlett., 2009, no. 14, p. 2217. https://doi.org/10.1055/s-0029-1217553
Saunthwal, R.K., Cornall, M.T., Abrams, R., Ward, J.W., and Clayden, J., Chem. Sci., 2019, vol. 10, no. 11, p. 3408. https://doi.org/10.1039/c8sc05263h
Lenarsic, R., Kocevar, M., and Polanc, S., J. Org. Chem., 1999, vol. 64, no. 7, p. 2558. https://doi.org/10.1021/jo9821170
Escobar, M.A., Valderrama, M., Daniliuc, C.D., and Rojas, R.S., J. Braz. Chem. Soc., 2016, vol. 27, no. 1, p. 194. https://doi.org/10.1039/C5QO00016E
Hirose, D., Gazvoda, M., Košmrlj, J., and Taniguchi, T., J. Org. Chem., 2018, vol. 83, no. 8, p. 4712. https://doi.org/10.1021/acs.joc.8b00486
Polanc, S.J., Heterocycl. Chem., 2005, vol. 42, no. 3, p. 401. https://doi.org/10.1002/jhet.5570420307
Kovac, A., Majce, V., Lenarsic, R., Bombek, S., Bostock, J.M., Chopra, I., Polanc, S., and Gobec, S., Bioorg. Med. Chem. Lett., 2007, vol. 17, no. 7, p. 2047. https://doi.org/10.1016/j.bmcl.2007.01.015
Hron, R.J., Jursic, B.S., and Neumann, D.M., Bioorg. Med. Chem., 2016, vol. 24, no. 23, p. 6183. https://doi.org/10.1016/j.bmc.2016.09.074
Urankar, D. and Košmrlj, J., Inorg. Chim. Acta, 2010, vol. 363, no. 14, p. 3817. https://doi.org/10.1016/j.ica.2010.07.031
Vajs, J., Pevec, A., Gazvoda, M., Urankar, D., Goreshnik, E., Polanc, S., and Košmrlj, J., Acta Chim. Slov., 2017, vol. 64, no. 4, p. 763. https://doi.org/10.17344/acsi.2017.3844
Hill, R.D. and Vederas, J.C., J. Org. Chem., 1999, vol. 64, no. 26, p. 9538. https://doi.org/10.1021/jo9915123
Nebel, N., Strauch, B., Maschauer, S., Lasch, R., Rampp, H., Fehler, S.K., Bock, L.R., Hübner, H., Gmeiner, P., Heinrich, M.R., and Prante, O., ACS Omega, 2017, vol. 2, no. 12, p. 8649. https://doi.org/10.1021/acsomega.7b01374
Nebel, N., Maschauer, S., Kuwert, T., Hocke, C., and Prante, O., Molecules, 2016, vol. 21, no. 9, p. 1144 https://doi.org/10.3390/molecules21091144
Dembitsky, V.M., Gloriozova, T.A., and Poroikov, V.V., Nat. Prod. Bioprospect., 2017, vol. 7, no. 1, p. 151. https://doi.org/10.1007/s13659-016-0117-3
Chan, W.Y., Ng, T.B., Lam, J.S.Y., Wong, J.H., Chu, K.T., Ngai, P.H.K., Lam,, S.K., and Wang, H.X., Appl. Microbiol. Biotechnol., 2010, vol. 85, no. 4, p. 985. https://doi.org/10.1007/s00253-009-2048-y
Mougin, С. and Veyland, A., Patent France 3020066, 2015.
Darnaud, C., Araujo, S.J.C., Longchambon, K., and Veyland, A., Patent WO 2012130884, 2012.
Korth, C., Keck, J., Erhardt, S., Monkiewicz, J., Springer, C., and Bauer, E., Patent US 2017174712, 2017.
Lagercrantz, C. and Deinum, J., Acta Chem. Scand., 1994, vol. 48, p. 670. https://doi.org/10.3891/acta.chem.scand.48-0670
Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, Butterworth-Heinemann: Elsevier, 2009.
Funding
This work was supported by the Russian Foundation for Basic Research (grant no. 19-03-00143) using analytical equipment of the Baikal Center for Collective Use of the SB RAS.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
No conflict of interest was declared by the authors.
Additional information
To the 100th Anniversary of M.G. Voronkov
Rights and permissions
About this article
Cite this article
Lazareva, N.F., Lazarev, I.M. N,N′-Bis(silylmethyl)azodicarboxamides. Russ J Gen Chem 91, 2412–2415 (2021). https://doi.org/10.1134/S1070363221120082
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363221120082