Upon reaction of N-anion of urea with 6-methoxy-1,3,7-triazapyrenes in DMSO at room temperature the products of nucleophilic ipso substitution of methoxy group with amino group form in high yields.
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Notes
Found, m/z: 316.0812 [М+Na]+. C15H11N5NaO2. Calculated, m/z: 316.0827.
References
(a) Corey, E. J.; Czako, B.; Kurti, L. Molecules and Medicine, Wiley: Hoboken, 2007, 272 pp. (b) Travis, A. S. In The Chemistry of Anilines, Patai Series, The Chemistry of Functional Groups, Rappoport, Z., Ed.; Wiley: Chichester, 2007, part 2, chap. 13, p. 715. (c) Amino Group Chemistry, From Synthesis to the Life Sciences, Ricci A., Ed.; Wiley-VCH: Weinheim, 2007, p. 207–256. (d) Gangopadhyay, P.; Radhakrishnan, T. P. Chem. Mater. 2000, 12, 3362. (e) Bag, B.; Bharadwaj, P. K. J. Phys. Chem. B 2005, 109, 4377.
Terrier, F. Modern Nucleophilic Aromatic Substitution. Weinheim: Wiley-VCH Verlag GmbH &Co. KGaA, 2013, 472 pp.
(a) Charushin, V. N.; Chupakhin, O. N. Top. Heterocycl. Chem. 2014, 37, 1. (b) Makosza, M.; Wojciechowski, K. Top. Heterocycl. Chem. 2014, 37, 51. (c) Gulevskaya, A. V.; Pozharskii, A. F. Top. Heterocycl. Chem. 2014, 37, 179.
Paudler, W. W.; Chen, T.-K. J. Org. Chem. 1971, 36, 787.
Ryabtsova, O.; Verhelst, T.; Baeten, M.; Vande Velde, C. M. L.; Maes, B. U. W. J. Org. Chem. 2009, 74, 9440.
Liao, T. K.; Nyberg, W. H.; Cheng, C. C. Angew. Chem., Int. Ed. Engl. 1967, 6, 82.
Denny, W. A.; Atwell, G. J.; Roberts, P. B.; Anderson, R. F.; Boyd, M.; Lock, C. J. L.; Wilson, W. R. J. Med. Chem. 1992, 35, 4832.
Borovlev, I.; Demidov, O.; Saigakova, N.; Amangasieva, G. Eur. J. Org. Chem. 2014, 7675.
Borovlev, I. V.; Demidov, O. P.; Kurnosova, N. A.; Amangasieva, G. A.; Avakyan E. K. Chem. Heterocycl. Compd. 2015, 51, 334. [Khim. Geterotsikl. Soedin. 2015, 51, 334.]
Artamkina, G. A.; Sergeev, A. G.; Shtern, M. M.; Beletskaya, I. P. Russ. J. Org. Chem. 2006, 42, 1683. [Zh. Org. Khim. 2006, 42 1695.]
Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512.
Demidov, O. P.; Borovlev, I. V.; Pisarenko, S. V.; Nemykina, O. A.; Saigakova, N. A. Chem. Heterocycl. Compd. 2010, 46, 636. [Khim. Geterotsikl. Soedin. 2010, 791.]
Saigakova, N. A; Demidov, O. P; Borovlev, I. V. Russ. J. Org. Chem. 2013, 49, 1199. [Zh. Org. Khim. 2013, 49, 1215.]
Borovlev, I. V.; Demidov, O. P.; Borovlev, I. I.; Saigakova, N. A. Chem. Heterocycl. Compd. 2013, 49, 952. [Khim. Geterotsikl. Soedin. 2013, 1018.]
Borovlev, I. V.; Demidov, O. P.; Saigakova N. A. Chem. Heterocycl. Compd. 2013, 49, 618. [Khim. Geterotsikl. Soedin. 2013, 662.]
This work was supported by funding from the Ministry of Education and Science of the Russian Federation, project № 4.141.2014/K.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(6), 586–588
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Amangasieva, G.A., Borovlev, I.V., Demidov, O.P. et al. Urea in an aminodemethoxylation reaction of 6-methoxy-1,3,7-triazapyrenes. Chem Heterocycl Comp 51, 586–588 (2015). https://doi.org/10.1007/s10593-015-1743-0
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DOI: https://doi.org/10.1007/s10593-015-1743-0