The reaction of 4-substituted anilines with 3,4,4-trichloro-1,1-bis(3,5-dimethyl-1H-pyrazol-1-yl)-2-nitrobuta-1,3-dienes led to 1-arylamino-3,4,4-trichloro-1-(3,5-dimethyl-1H-pyrazol-1-yl)-2-nitrobuta-1,3-dienes, which under the action of 2-aminopyridines underwent heterocyclization to the corresponding 2-arylamino-substituted 4-(dichloromethylidene)-3-nitro-4H-pyrido[1,2-a]pyrimidines. The molecular structure of 4H-pyrido[1,2-a]pyrimidine containing the (4-ethoxyphenyl)amine substituent at position 2 was determined by X-ray structural analysis.
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(a) Kapui, Z.; Varga, M.; Urban-Szabo, K.; Mikus, E.; Szabo, T.; Szeredi, J.; Batori, S.; Finance, O.; Aranyi, P. J. Pharmacol. Exp. Ther. 2003, 305, 451. (b) Banjanac, M.; Tatic, I.; Ivezic, Z.; Tomic, S.; Dumic, J. Food Technol. Biotechnol. 2009, 47, 236. (c) La Motta, C.; Sartini, S.; Mugnaini, L.; Simorini, F.; Taliani, S; Salerno, S; Marini, A. M; Da Settimo, F; Lavecchia, A.; Novellino, E.; Cantore, M.; Failli, P.; Ciuffi, M. J. Med. Chem. 2007, 50, 4917. (d) Rauf, A.; Liaqat, S.; Qureshi, A. M.; Yaqub, M.; Rehman, A. U.; Hassan, M. U.; Chohan, Z. H.; Nasim, F. U. H.; Ben Hadda, T. Med. Chem. Res. 2012, 21, 60. (e) Arutyunyan, А. А.; Gasparyan, G. V.; Sukasyan, R. S.; Grigoryan, А. S. Khim. Zh. Armenii 2016, 69, 362.
(a) Ukrainets, I. V.; Bereznyakova, N. L.; Tugaibei, I. A. Chem. Heterocycl. Compd. 2008, 44, 50. [Khim. Geterotsikl. Soedin. 2008, 61.] (b) Ukrainets, I. V. Taran, E. А. Bereznyakova, N. L. Zh. Org. Farm. Khim. 2014, 12, 65. b Alwan, S. M.; Abdul-Sahib Al-Kaabi, J.; Hashim, R. M. M. Med. Chem. 2014, 4, 635. c Vartale, S. P.; Halikar, N. K.; Jadhav, A. G.; Chavan, S. B.; Patwari, S. B. Scholars Acad. J. Pharm. 2013, 2, 130. d Fenton, C.; Scott, L. J. CNS Drugs 2005, 19, 429.
(a) Badawy, D. S.; Awad, N. M.; Abdel-Galil, E. J. Heterocycl. Chem. 2013, 50, 1351. (b) Hamama, W. S.; Zoorob, H. H. Tetrahedron 2002, 58, 6143.
Zapol'skii, V. A.; Namyslo, J. C.; de Meijere, A.; Kaufmann, D. E. Beilstein J. Org. Chem. 2012, 8, 621.
Kolesnyk, I. A.; Petkevich, S. K.; Tsaryk, A. D.; Kurman, P. V.; Potkin, V. I. Russ. J. Org. Chem. 2020, 56, 20. [Zh. Org. Khim. 2020, 56, 31.]
Zapol'skii, V. А.; Potkin, V. I.; Nechai, N. I.; Kaberdin, R. V.; Pevzner, M. S. Zh. Org. Khim. 1997, 33, 1541.
(a) Zapol'skii, V. A.; Namyslo, J. C.; Altug, C.; Gjikaj, M.; Kaufmann, D. E. Synthesis 2008, 304. (b) Zapol'skii, V. A.; Namyslo, J. C.; Gjikaj, M.; Kaufmann, D. E. Beilstein J. Org. Chem. 2014, 10, 1638. (c) Zapol'skii, V. A.; Vogt, E.-J.; Gjikaj, M.; Kaufmann, D. E. Heterocycles 2012, 86, 1431. (d) Zapol'skii, V. A.; Namyslo, J. C.; Adam, A. E. W.; Gjikaj, M.; Kaufmann, D. E. Heterocycles 2004, 63, 1281.
Takhistov, V. V. Organicheskaya mass-spektrometriya (Organic Mass Spectrometry [in Russian]); Leningrad: Nauka, 1990.
Steyermark, A. Quantitative Organic Microanalysis; Academic Press: New York, 1961.
Burla, M. C.; Caliandro, R.; Carrozzini, B.; Cascarano, G. L.; Cuocci, C.; Giacovazzo, C.; Mallamo, M.; Mazzone, A.; Polidori, G. J. Appl. Crystallogr. 2015, 48, 306.
Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.
Spek, A. L. Acta Crystallogr., Sect. D: Struct. Biol. 2009, D65, 148.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1187–1192
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Kolesnik, I.А., Petkevich, S.K., Kurman, P.V. et al. Synthesis and Structure of 2-Arylamino-Substituted 4-(Dichloromethylidene)-3-Nitro-4h-Pyrido[1,2-a]Pyrimidines. Chem Heterocycl Comp 56, 1187–1192 (2020). https://doi.org/10.1007/s10593-020-02796-0
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DOI: https://doi.org/10.1007/s10593-020-02796-0