The reaction of 4-amino-8-hydroxy-1,6-dioxo-2,7-diazaspiro[4.4]non-3-ene-4-carbonitriles with Lawesson's reagent proceeded as an iminothiolactone-thiolactam rearrangement, leading to the formation of 4-amino-6-thioxo-3,7,9-triazatricyclo[6.2.1.01,5]undec-4-ene-2,10-diones.
Similar content being viewed by others
References
Song, Z.-L.; Fan, C.-A.; Tu, Y.-Q. Chem. Rev. 2011, 111, 7523.
Tejedor, D.; Méndez-Abt, G.; Cotos, L.; García-Tellado, F. Chem. Soc. Rev. 2013, 42, 458.
Métro, T.-X.; Duthion, B.; Pardo, D. G.; Cossy, J. Chem. Soc. Rev. 2010, 39, 89.
Gómez, A. M.; Lobo, F.; Uriel, C.; López J. C. Eur. J. Org. Chem. 2013, 32, 7221.
Tabolin, A. A.; Ioffe, S. L. Chem. Rev. 2014, 114, 5426.
Snape, T. J. Chem. Soc. Rev. 2008, 37, 2452.
Kayukov, Ya. S.; Bardasov, I. N.; Karpov, S. V.; Ershov, O. V.; Nasakin, O. E.; Kayukova, O. V.; Tafeenko, V. A. Russ. J. Org. Chem. 2012, 48, 1447. [Zh. Org. Khim. 2012, 48, 1463.]
Bardasov, I. N.; Alekseeva, A. U.; Mihailov, D. L.; Ershov, O. V.; Nasakin, O. E.; Tafeenko, V. A. Tetrahedron Lett. 2014, 55, 2730.
Han, Y.; Tang, W.-Q.; Guo, L.-Y.; Yan, C.-G. Tetrahedron 2014, 70, 6663.
Angelin, M.; Vongvilai, P.; Fischera, A.; Ramström, O. Chem. Commun. 2008, 768.
Song, Y. S.; Lee, C. H.; Lee, K.-J. J. Heterocycl. Chem. 2003, 40, 939.
Palombi, L.; Molab, A. D.; Massa, A. New J. Chem. 2015, 39, 81.
Wu, X.-F.; Oschatz, S.; Block, A.; Spannenbergb, A.; Langer, P. Org. Biomol. Chem. 2014, 12, 1865.
Ghozlan, S. A. S.; Abdelmoniem, D. M.; Mady, M. F.; Abdelmoniem, A. M.; Abdelhamid, I. A. Heterocycles 2016, 92, 637.
Hilmy, K. M. H.; Soliman, D. H.; Shahin, E. B. A.; El-Deeb, H. S.; El-Kousy, S. M. Eur. J. Med. Chem. 2014, 78, 419.
Briel, D.; Aurich, R.; Egerland, U.; Unverferth, K. Pharmazie 2005, 60(10), 732.
Fathalla, W. M.; Pazdera P. Molecules. 2002, 7, 96.
Karlivan, G. A.; Valter, R. E.; Bace, A. E. Chem. Heterocycl. Compd. 1999, 35, 866. [Khim. Geterotsikl. Soedin. 1999, 988.]
Kambe, T.; Maruyama, T.; Nagase, T.; Ogawa, S.; Minamoto, Ch.; Sakata, K.; Maruyama, T.; Nakai, H.; Toda, M. Bioorg. Med. Chem. 2012, 20, 702.
Luo, W.; Yu, Q.-Sh.; Salcedo, I.; Holloway, H. W.; Lahiri, D. K.; Brossi, A.; Tweedie, D.; Greig, N. H. Bioorg. Med. Chem. 2011, 19, 3965.
Orzesko, A.; Vilpo, J.; Kaminska, B. Pharmazie 2003, 58, 169.
Di Pardo, R. M.; Patane, M. A.; Newton, R. C.; Price, R. A.; Broten, T. P.; Chang, R. S. L.; Ransom, R. W.; Di Salvo, J.; Freidinger, R. M.; Bock, M. G. Bioorg. Med. Chem. Lett. 2001, 11, 1959.
Fedoseev, S. V.; Ershov, O. V.; Belikov, M. Yu.; Lipin, K. V.; Bardasov, I. N.; Nasakin, O. E.; Tafeenko, V. A. Tetrahedron Lett. 2013, 54, 2143.
Fedoseev, S. V.; Ershov, O. V.; Lipin, K. V.; Belikov, M. Yu. RSC Adv. 2016, 6, 10597.
Fedoseev, S. V.; Lipin, K. V.; Ershov, O. V.; Belikov, M. Yu.; Tafeenko, V. A. Russ. J. Org. Chem. 2016, 52, 1606. [Zh. Org. Khim. 2016, 52, 1613.]
Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2007, 107, 5210.
Belikov, M. Yu.; Belikova, I. V.; Ershov, O. V.; Fedoseev, S. V. Russ. J. Org. Chem. 2016, 52, 1854. [Zh. Org. Khim. 2016, 52, 1860.]
Eremkin, A. V.; Ershov, O. V.; Davydova, V. V.; Nasakin, O. E. Russ. J. Org. Chem. 2015, 51, 1813. [Zh. Org. Khim. 2015, 51, 1846.]
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.
Brandenburg, K. DIAMOND, Release 2.1d; Crystal Impact GbR: Bonn, 2000.
The study was performed within the framework of scholarship SP-2802.2015.4 awarded by the President of the Russian Federation to young scientists and graduate students.
The X-ray structural studies were performed by using equipment of the Chair of General Chemistry, Faculty of Chemistry, M. V. Lomonosov Moscow State University.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(9), 1045–1049
Electronic supplementary material
ESM 1
(PDF 1089 kb)
Rights and permissions
About this article
Cite this article
Fedoseev, S.V., Belikov, M.Y., Ershov, O.V. et al. Iminothiolactone-thiolactam rearrangement in the synthesis of 4-amino-6-thioxo-3,7,9-triazatricyclo-[6.2.1.01,5]undec-4-ene-2,10-diones. Chem Heterocycl Comp 53, 1045–1049 (2017). https://doi.org/10.1007/s10593-017-2167-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-017-2167-9