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Amides of 1,3,7-triazapyrene series: synthesis by nucleophilic substitution of alkoxy groups

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Chemistry of Heterocyclic Compounds Aims and scope

The treatment of 6,8-dialkoxy-1,3,7-triazapyrenes with sodium acylamides in DMSO at room temperature resulted in ipso substitution of one alkoxy group with amide group, giving 8-acylamino-6-alkoxy-1,3,7-triazapyrenes. The reaction at 65–70°C proceeded as a tandem SNAripso–SN2 process, leading to the formation of 8-acylamino-6-oxo-6,7-dihydro-1,3,7-triazapyrenes.

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References

  1. (a) Corey, E. J.; Czakó, B.; Kürti, L. Molecules and Medicine; Wiley: Hoboken, 2007. (b) Travis, A. S. In The Chemistry of Anilines, Patai Series, The Chemistry of Functional Groups; Rappoport, Z., Ed.; Wiley: Chichester, 2007, pt. 2, chap. 13, p. 715. (c) Amino Group Chemistry, From Synthesis to the Life Sciences; Ricci A., Ed.; Wiley-VCH: Weinheim, 2007. (d) Gangopadhyay, P.; Radhakrishnan, T. P. Chem. Mater. 2000, 12, 3362. (e) Bag, B.; Bharadwaj, P. K. J. Phys. Chem. B 2005, 109, 4377. (f) Kubicek, S.; O'Sullivan, R. J.; August, E. M.; Hickey, E. R.; Zhang, Q.; Teodoro, M. L.; Rea, S.; Mechtler, K.; Kowalski, J. A.; Homon, C. A.; Kelly, T. A.; Jenuwein, T. Mol. Cell 2007, 25, 473.

  2. Gorelik, M. V.; Efros, L. S. Fundamentals of Chemistry and Technology of Aromatic Compounds [in Russian]; Khimiya: Moscow, 1992.

    Google Scholar 

  3. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (b) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. (c) Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338. (d) Surry, D. S.; Buchwald, S. L. Angew. Chem. 2008, 120, 6438. (e) Roiban, G.-D.; Mehler, G.; Reetz, M. T. Eur. J. Org. Chem. 2014, 2070.

  4. (a) Kim, J.; Kim, J.; Chang, S. Chem.–Eur. J. 2013, 19, 7328. (b) Ryu, J.; Shin, K.; Park, S. H.; Kim, J. Y.; Chang, S. Angew. Chem. 2012, 124, 10042. c) Ryu, J.; Shin, K.; Park, S. H.; Kim, J. Y.; Chang, S. Angew. Chem., Int. Ed. 2012, 51, 9904. (d) Shi, J.; Zhou, B.; Yang, Y.; Li, Y. Org. Biomol. Chem. 2012, 10, 8953.

  5. Wang, Q. S.; Schreiber L. Org. Lett. 2009, 11, 5178.

    Article  CAS  Google Scholar 

  6. (a) Stern, M. K.; Cheng, B. K. J. Org. Chem. 1993, 58, 6883. (b) Stern, M. K.; Bashkin, K. J. US Patent 5117063. (c) Gulevskaya, A. V.; Tyaglivaya, I. N.; Verbeeck, S.; Maes, B. U. W.; Tkachuk, A. V. ARKIVOC 2011, (ix), 238.

  7. Borovlev, I. V; Demidov, O. P; Kurnosova, N. A; Amangasieva, G. A.; Avakyan, E. K. Chem. Heterocycl. Compd. 2015, 51, 170. [Khim. Geterotsikl. Soedin. 2015, 51, 170.]

  8. (a) Borovlev, I. V.; Demidov, O. P.; Saigakova, N. A. Russ. Chem. Bull., Int. Ed. 2011, 60, 1784. [Izv. Akad. Nauk, Ser. Khim. 2011, 1755.] (b) 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.]

  9. (a) Paudler, W. W.; Chen, T.-K. J. Org. Chem. 1971, 36, 787. (b) Ryabtsova, O.; Verhelst, T.; Baeten, M.; Vande Velde, C. M. L.; Maes, B. U. W. J. Org. Chem. 2009, 74, 9440. (c) Liao, T. K.; Nyberg, W. H.; Cheng, C. C. Angew. Chem., Int. Ed. 1967, 6, 82. (d) 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.

  10. (a) Borovlev, I. V.; Demidov, O. P.; Saigakova, N. A. Chem. Heterocycl. Compd. 2014, 50, 685. [Khim. Geterotsikl. Soedin. 2014, 746.] (b) Borovlev, I.; Demidov, O.; Saigakova, N.; Amangasieva, G. Eur. J. Org. Chem. 2014, 7675.

  11. Saigakova, N. A.; Demidov, O. P.; Borovlev, I. V. Russ. J. Org. Chem. 2013 , 49, 1199. [Zh. Org. Khim. 2013, 49, 1215.].

  12. (a) Sauer, S.; Huisgen, R. Angew. Chem. 1960, 72, 294. (b) Daniels, R.; Grady, L. T.; Bauer, L. J. Am. Chem. Soc. 1965, 87, 1531.

  13. Demidov, O. P.; Borovlev, I. V.; Saigakova, N. A.; Nemykina, O. A.; Pisarenko, S. V. Chem. Heterocycl. Compd. 2013, 48, 1527. [Khim. Geterotsikl. Soedin. 2012, 1639.]

  14. Minkin, V. I.; Garnovskii, A. D.; Elguero, J.; Katritzky, A. R.; Denisko, O. V. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Elsevier: New York, 2000, vol. 76, p. 157.

    CAS  Google Scholar 

  15. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512.

    Article  CAS  Google Scholar 

  16. Sharp, J.T.; Gosney, I.; Rowley, A. G. Practical Organic Chemistry [Russian translation, Moskva, V. V., Ed.]; Mir: Moscow, 1993, p. 188.

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This work received financial support from the Ministry of Education and Science of the Russian Federation (project No. 4.141.2014/K).

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Correspondence to Ivan V. Borovlev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(4), 334–339

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Borovlev, I.V., Demidov, O.P., Kurnosova, N.A. et al. Amides of 1,3,7-triazapyrene series: synthesis by nucleophilic substitution of alkoxy groups. Chem Heterocycl Comp 51, 334–339 (2015). https://doi.org/10.1007/s10593-015-1704-7

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  • DOI: https://doi.org/10.1007/s10593-015-1704-7

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