It was shown that 3-amino-4-cyanofurazan easily condenses with malononitrile and ethyl cyanoacetate in the presence of bases, forming polyfunctional enaminonitriles – precursors in the synthesis of pyrazoles and annulated derivatives of furazano[3,4-b]pyridines and furazano[3,4-b]pyrimidines.
Similar content being viewed by others
References
(a) Rulev, A. Yu. Russ. Chem. Rev. 2002, 71, 195. [Usp. Khim. 2002, 71, 225.] (b) Elassar, A.-Z. A.; El-Khair, A. A. Tetrahedron 2003, 59, 8463.
(a) Granik, V. G.; Makarov, V. A.; Parkanyi, C. Adv. Heterocycl. Chem. 1998, 72, 283. (b) Riyadh, S. M.; Abdelhamid, I. A.; Al-Matar, H. M.; Hilmy, N. M.; Elnagdi, M. H. Heterocycles 2008, 75, 1849. (c) Bondock, S.; Tarhoni, A. El-G.; Fadda, A. A. Curr. Org. Chem. 2011, 15, 753. (d) Alekseeva, A. Yu.; Bardasov, I. N. Chem. Heterocycl. Compd. 2018, 54, 689. [Khim. Geterotsikl. Soedin. 2018, 54, 689.] (e) Stanovnik, B. Eur. J. Org. Chem. 2019, 5120. e Dar’in, D. V.; Lobanov, P. S. Russ. Chem. Rev. 2015, 84, 601. [Usp. Khim. 2015, 84, 601.] (g) Erian, A. W. Chem. Rev. 1993, 93, 1991.
(a) Vasil’ev, L. S.; Sheremetev, A. B.; Dorokhov, V. A.; Khoa, N. K.; Dekaprilevich, M. O.; Struchkov, Yu. T.; Khmel’nitskii, L. I. Mendeleev Commun. 1994, 4, 57. (b) Vasil’ev, L. S.; Sheremetev, A. B.; Khoa, N. K.; Dem’yanets, Z. K.; Dmitriev, D. E.; Dorokhov, V. A. Russ. Chem. Bull. 2001, 1280. [Izv. Akad. Nauk, Ser. Khim. 2001, 1220.]
Andrianov, V. G.; Eremeev, A. V. Chem. Heterocycl. Compd. 1994, 30, 608. [Khim. Geterotsikl. Soedin. 1994, 693.]
(a) Godbout, C.; Trieselmann, T.; Vintonyak, V. WO Patent 2018/024653. (b) Godbout, C.; Trieselmann, T.; Vintonyak, V. WO Patent 2019/149657. (c) Godbout, C.; Trieselmann, T.; Vintonyak, V. WO Patent 2019/149658. (d) Godbout, C.; Trieselmann, T.; Vintonyak, V. WO Patent 2019/149659.
Vasilev, L. S.; Sheremetev, A. B.; Dorokhov, V. A.; Suponitsky, K. Yu. J. Heterocycl. Chem. 2007, 44, 843.
(a) Junek, H.; Thierrichter, B.; Lukas, G. Chem. Ber. 1980, 113, 1195. (b) Zaki, M. E. A.; Proença, M. F.; Booth, B. L. J. Org. Chem. 2003, 68, 276. (c) Khodairy, A. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 1893. (d) Mohareb, R. M.; Fleita, D. H.; Sakka, O. K. Heterocycl. Commun. 2011, 17, 25. (e) Hassan, A. A.; El-Shaieb, K. M. A.; Mohamed, N. K.; Tawfeek, H. N.; Bräse, S.; Nieger, M. Tetrahedron Lett. 2014, 55, 2385. (f) Tverdokhleb, N. M.; Khoroshilov, G. E.; Dotsenko, V. V. Tetrahedron Lett. 2014, 55, 6593. (g) Hassan, A. A.; Mohamed, N. K.; El-Shaieb, K. M. A.; Tawfeek, H. N.; Bräse, S.; Nieger, M. ARKIVOC 2016, (vi), 163. g Al-duaij, O. K.; Zaki, M. E. A.; El Gazzar, A.-R. B. A. Molecules 2016, 21, 1646.
Vnutrimolekulyarnoe vzaimodeistvie nitril’noi i aminogrupp (Intramolecular Reactions of Nitrile and Amino Groups [in Russian]); Babichev, F. S.; Sharanin, Yu. А.; Promonenkov, V. K.; Litvinov, V. P.; Volovenko, Yu. M., Ed.; Kiev: Naukova Dumka, 1987, p. 57.
(a) Rewcastle, G. W. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier, 2008, Vol. 8, p. 117. a Koroleva, E. V.; Gusak, K. N.; Ignatovich, Zh. V. Russ. Chem. Rev. 2010, 79, 655. [Usp. Khim. 2010, 79, 720.]
(a) Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170. (b) Espinosa, E.; Alkorta, I.; Rozas, I.; Elguero, J.; Molins, E. Chem. Phys. Lett. 2001, 336, 457.
(a) Dmitrienko, A. O.; Karnoukhova, V. A.; Potemkin, A. A.; Struchkova, M. I.; Kryazhevskikh, I. A.; Suponitsky, K. Yu. Chem. Heterocycl. Compd. 2017, 53, 532. [Khim. Geterotsikl. Soedin. 2017, 53, 532.] (b) Sheremetev, A. B.; Aleksandrova, N. S.; Semyakin, S. S.; Suponitsky, K. Yu.; Lempert, D. B. Chem.–Asian J. 2019, 14, 4255. b Suponitsky, K. Yu.; Lyssenko, K. A.; Ananyev, I. V.; Kozeev, A. M.; Sheremetev, A. B. Cryst. Growth Des. 2014, 14, 4439.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(8), 1003–1107
Electronic supplementary material
ESM 1
(PDF 994 kb)
Rights and permissions
About this article
Cite this article
Strizhenko, K.V., Vasil’ev, L.S., Suponitsky, K.Y. et al. 3-Amino-4-(1-amino-2-cyanovinyl)furazans: synthesis and cyclization. Chem Heterocycl Comp 56, 1103–1107 (2020). https://doi.org/10.1007/s10593-020-02781-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-020-02781-7