The reaction between dehydrobenzene and tetrahydropyrido[4,3-d]pyrimidin-4-ones condensed with isoxazole, thiazole, thiadiazole, or triazole rings resulted in Hofmann cleavage of the tetrahydropyridine moiety with the formation of 6-vinyl-substituted pyrimidones fused with the corresponding azole rings.
Similar content being viewed by others
References
Voskressensky, L. G.; Kovaleva, S. A.; Borisova, T. N.; Eresko, A. B.; Tolkunov, V. S.; Listratova, A. V.; de Candia, M.; Altomare, C.; Varlamov, A. V. Chem. Heterocycl. Compd. 2013, 49, 930. [Khim. Geterotsikl. Soedin. 2013, 995.]
Voskressensky, L. G.; Borisova, T. N.; Kulikova, L. N.; Varlamov, A. V.; Catto, M.; Altomare, C.; Carotti, A. Eur. J. Org. Chem. 2004, 3128.
Voskressensky, L. G.; Borisova, T. N.; Chervyakova, T. M.; Titov, A. A.; Kozlov, A. V.; Sorokina, E. A.; Samavati, R.; Varlamov, A. V. Chem. Heterocycl. Compd. 2014, 50, 658. [Khim. Geterotsikl. Soedin. 2014, 716.]
Voskressensky, L. G.; Borisova, T. N.; Chervyakova, T. M.; Matveeva, M. D.; Galaktionova, D. V.; Tolkunov, S. V.; Tolkunova, V. S.; Eresko, A. B.; Varlamov, A. V. Chem. Heterocycl. Compd. 2014, 50, 1338. [Khim. Geterotsikl. Soedin. 2014, 1451.]
Voskressensky, L. G.; Listratova, A. V.; Borisova, T. N.; Kovaleva, S. A.; Borisov, R. S.; Varlamov, A. V. Tetrahedron 2008, 64, 10443.
Voskressensky, L. G.; Listratova, A. V.; Borisova, T. N.; Alexandrov, A. A.; Varlamov, A. V. Eur. J. Org. Chem. 2007, 6106.
Carotti, A.; de Candia, M.; Catto, M.; Borisova, T. N.; Varlamov, A. V.; Méndez-Álvares, E.; Soto-Otero, R.; Voskressensky, L. G.; Altomare, C. Bioorg. Med. Chem. 2006, 14, 7205.
Voskressensky, L. G.; Borisova, T. N.; Kostenev, I. S.; Kulikova, L. N.; Varlamov, A. V. Tetrahedron Lett. 2006, 47, 999.
Voskressensky, L. G.; Borisova, T. N.; Ovcharov, M. V.; Sorokina, E. A.; Khrustalev, V. N.; Varlamov, A. V. Russ. Chem. Bull., Int. Ed. 2012, 61, 1603. [Izv. Akad. Nauk, Ser. Khim. 2012, 1587.]
Ovcharov, M. V. Dissertation of Candidate of Chemical Sciences; Moscow, 2010.
Voskressensky, L. G.; Borisova, T. N.; Ovcharov, M. V.; Kulikova, L. N.; Sorokina, E. A.; Borisov, R. S.; Varlamov, A. V. Chem. Heterocycl. Compd 2008, 44, 1510. [Khim. Geterotsikl. Soedin. 2008, 1861.]
Purification of Laboratory Chemicals; Armarego, W. L. F.; Chai, C., Eds.; Elsevier Butterworth-Heinemann, 2003, p. 85.
This study received financial support from Project RUDN 5-100 for years 2016–2020 and the Russian Foundation for Basic Research (grant 17-03-00605).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(2), 173–176
Rights and permissions
About this article
Cite this article
Varlamov, A.V., Guranova, N.I., Borisova, T.N. et al. Interaction of condensed tetrahydropyrido[4,3-d]pyrimidin-4-ones with dehydrobenzene – synthesis of 6-vinylpyrimidinones fused with five-membered heterocycle containing two or three heteroatoms. Chem Heterocycl Comp 54, 173–176 (2018). https://doi.org/10.1007/s10593-018-2250-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-018-2250-x