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Dimroth rearrangement in the synthesis of substituted cyclopentaand cyclohexa[4,5]thieno[2',3':4,5]pyrimido[1,6-b][1,2,4]triazines

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Chemistry of Heterocyclic Compounds Aims and scope

A simple and effective method has been developed for the synthesis of previously unknown cyclopenta- and cyclohexa[4',5']thieno-[2',3':4,5]pyrimido[1,6-b][1,2,4]triazines in a single step by reaction of 4-hydrazinocyclopenta- and 4-hydrazinocyclohexa[4,5]thieno-[2,3-d]pyrimidines with sodium salts of methyl 4-aryl(heteryl)-2,4-dioxobutanoates. It was shown that the determining factor in the formation of tetracyclic products was isomerization by intramolecular recyclization with mechanism analogous to the Dimroth rearrangement.

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References

  1. (a) Khripak, S. M.; Slivka, M. V.; Lendel, V. G. Synthesis and Properties of Thieno[2,3-d]pyrimidines [in Ukrainian]; VAT Paten: Uzhgorod, 2009. (b) Abdelhamid, A. O.; El-Idreesy, T. T.; Abdelriheem, N. A.; Dawoud, H. R. M. J. Heterocycl. Chem. 2016, 53, 710. (c) Kassab, A. E.; Gedawy, E. M.; El-Malah, A. A.; Abdelghany, T. M.; Abdel-Bakky, M. S. Chem. Pharm. Bull. 2016, 64, 490. (d) Paronikyan, E. G.; Dashyan, S. S.; Minasyan, N. S.; Stepanyan, G. M. Russ. J. Org. Chem. 2016, 52, 576. [Zh. Org. Khim. 2016, 52, 589.] (e) Sirakanyan, S. N.; Spinelli, D.; Geronikaki, A.; Panosyan, H. A.; Hovakimyan, A. A. Curr. Org. Chem. 2016, 20, 1350. (f) Paronikyan, E. G.; Dashyan, Sh. Sh.; Noravyan, A. S.; Minasyan, N. S. Chem. Heterocycl. Compd. 2014, 50, 1188. [Khim. Geterotsikl. Soedin. 2014, 1286.] (g) Voskressensky, L. G.; Kovaleva, S. A.; Borisova, T. N.; Titov, A. A.; Toze, F.; Listratova, A. V.; Khrustalev, V. N.; Varlamov, A. V. Chem. Heterocycl. Compd. 2015, 51, 17. [Khim. Geterotsikl. Soedin. 2015, 51, 17.] (h) Paronikyan, E. G.; Dashyan, Sh. Sh.; Minasyan, N. S.; Stepanyan, G. M.; Babaev, E. V. Chem. Heterocycl. Compd. 2016, 52, 337. [Khim. Geterotsikl. Soedin. 2016, 52, 337.]

  2. (a) Abdel Aziz, Y. M.; Said, M. M.; El Shihawy, H. A.; Abouzid, K. A. M. Bioorg. Chem. 2015, 60, 1. (b) Gryshchenko, A. A.; Bdzhola, V. G.; Balanda, A. O.; Briukhovetska, N. V.; Kotey, I. M.; Golub, A. G.; Yarmoluk, S. M. Bioorg. Med. Chem. 2015, 23(9), 2287. (c) Kim, H.; Lee, C.; Yang, J. S.; Choi, S.; Park, C.; Kang, J. S.; Han, G. Eur. J. Med. Chem. 2016, 120, 74. (d) Al-Taisan K. M., Al-Hazimi, H. M. A.; Al-Shihry, S. S. Molecules 2010, 15, 3932. (e) Yong, J.; Lu, C.; Wu, X. Anti-Cancer Agents Med. Chem. 2015, 15, 1148. (f) Yu, M.; Li, P.; Basnet, S. K. C.; Kumarasiri, M.; Diab, S.; Teo, T.; Albrecht, H.; Wang, S. Eur. J. Med. Chem. 2015, 95, 116. (g) Petrie, C. R., Cottam, H. B.; McKernan, P. A.; Robins, R. K.; Revankar, G. R. J. J. Med. Chem. 1985, 28, 1010. (h) Alagarsamy, V.; Vijayakumar, S.; Raja Solomon, V. Biomed. Pharmacother. 2007, 61, 285. (i) Bhuiyan, M. H.; Rahman, K. M.; Hossain, K.; Rahim, A.; Hossain, M. I.; Naser, M. A. Acta Pharm. 2006, 56, 441.

  3. Kolomieitsev, D. O.; Markov, V. I.; Astakhina, V. O.; Kovalenko, S. I.; Varenichenko, S. A.; Kharchenko, O. V. Zh. Org. Farm. Khimii 2015, 13(4), 32.

    CAS  Google Scholar 

  4. 4. Robba, M.; Touzot, P.; Riquelme, R. M. C. R. Seances Acad. Sci., Ser. C 1973, 276, 93.

    CAS  Google Scholar 

  5. Gajda, K.; Astakhina, V.; Ejsmont, K.; Kolomeitsev, D.; Kovalenko, S.; Zarychta, B. J. Mol. Struct. 2015, 1083, 137.

    Article  CAS  Google Scholar 

  6. Vishnu Ji Ram Arch Pharm. (Weinheim, Ger.) 1979, 312, 19.

  7. Karpenko, O. V.; Kovalenko, S. I.; Chekotylo, O. O.; Shishkina, S. V. Heterocycles 2007, 71, 619.

    Article  CAS  Google Scholar 

  8. Karpenko, A. V.; Kovalenko, S. I.; Shishkin, O. V. Tetrahedron 2009, 65, 5964.

    Article  CAS  Google Scholar 

  9. Bakharev, V. V.; Parfenov, V. E.; Ul'yankina, I. V.; Zavodskaya, A. V.; Gidaspov, A. A.; Slepukhin, P. A. Chem. Heterocycl. Compd. 2015, 51, 1014. [Khim. Geterotsikl. Soedin. 2015, 51, 1014.]

  10. (a) Amer, A.; Zimmer, H. J. Heterocycl. Chem. 1983, 20, 1231. (b) Amer, A.; Weisz, K.; Zimmer, H. Heterocycles 1987, 26, 1853. (c) Rashed, N.; El Massry, A. M.; El Ashry, E. S. H.; Amer, A.; Zimmer, H. J. Heterocycl. Chem. 1990, 27, 691.

  11. Kolomieitsev, D. O.; Markov, V. I.; Astakhina, V. O.; Kovalenko, S. I.; Varenichenko, S. A.; Kharchenko, O. V. Voprosy Khimii i Khim. Tekhnologii 2016, (2), 32.

  12. (a) Dawood, K. M.; Abdel-Gawad, H.; Mohamed, H. A.; Abdel-Wahab, B. F. Heterocycles 2010, 81, 1. (b) Eftekhari-Sis, B.; Zirak, M. Chem. Rev. 2015, 115, 151. (c) Nolsöe, J. M. J.; Weigelt, D. J. Heterocycl. Chem. 2009, 46, 1.

  13. Kovalenko, S. I.; Karpenko, A. V.; Krivoshey, O. V.; Shishkina, S. V.; Shishkin, O. V. Synth. Commun. 2007, 37, 3719.

    Article  CAS  Google Scholar 

  14. 14. Abu-Zied, Kh. M.; Hussein, H. A. R.; Abu-Hashem, A. A. Org. Chem.: Indian J. 2012, 8(6), 211.

    CAS  Google Scholar 

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The work was performed with financial support from the Ministry of Education and Science of Ukraine within the State budget item No. 0115U003159 ''New Synthetic Methods for the Design of Nitrogen- and Sulfur-containing Biologically Active Compounds''.

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Authors and Affiliations

  1. Ukrainian State University of Chemical Technologies, 8 Gagarina Ave., Dnipro, 49005, Ukraine

    Dmitriy O. Kolomieitsev, Victor I. Markov, Svetlana A. Varenichenko, Valeriya O. Astakhina & Alexandr V. Kharchenko

  2. Zaporozhye State Medical University, 26 Mayakovsky Ave., Zaporozhye, 69035, Ukraine

    Sergiy I. Kovalenko

  3. A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, 86 Lustdorfskaya Road, Odessa, 65080, Ukraine

    Alexandr V. Mazepa

Authors
  1. Dmitriy O. Kolomieitsev
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  2. Victor I. Markov
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  3. Svetlana A. Varenichenko
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  4. Valeriya O. Astakhina
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  5. Sergiy I. Kovalenko
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  6. Alexandr V. Kharchenko
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  7. Alexandr V. Mazepa
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Corresponding author

Correspondence to Svetlana A. Varenichenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(7), 498–502

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Kolomieitsev, D.O., Markov, V.I., Varenichenko, S.A. et al. Dimroth rearrangement in the synthesis of substituted cyclopentaand cyclohexa[4,5]thieno[2',3':4,5]pyrimido[1,6-b][1,2,4]triazines. Chem Heterocycl Comp 52, 498–502 (2016). https://doi.org/10.1007/s10593-016-1915-6

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  • DOI: https://doi.org/10.1007/s10593-016-1915-6

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