Skip to main content
SpringerLink
Log in

Synthesis of nitromethyl-, N-methylindolyl-, or N-methylindolylnitromethyl-substituted 1,4-benzothiazin(diazin)ones and 3-methyl-1,4-benzoxazinones from alkyl 3-nitroacrylates

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reactions of alkyl 3-nitroacrylates and ethyl 2-(1-methyl-1H-indol-3-yl)-3-nitroacrylate with о-aminothiophenol, о-aminophenol, о-phenylenediamine, and their substituted analogs were used for the preparation of 2-(nitromethyl)-2H-1,4-benzothiazin-3(4H)-one, 2-(1-methyl-1H-indol-3-yl)-2-(nitromethyl)-2H-1,4-benzothiazin-3(4H)-one, 3-methyl-2H-1,4-benzoxazin-2-ones, and 3-(1-methyl-1H-indol-3-yl)quinoxalin-2(1H)-ones that were structurally characterized.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1.

Similar content being viewed by others

References

  1. Gupta, D.; Ghosh, N. N.; Chandra, R. Bioorg. Med. Chem. Lett. 2005, 15, 1019.

    Article  CAS  PubMed  Google Scholar 

  2. Tawada, H.; Sugiyama, Y.; Ikeda, H.; Yamamoto, Y.; Meguro, K. Chem. Pharm. Bull. 1990, 38, 1238.

    Article  CAS  PubMed  Google Scholar 

  3. Matsui, T.; Nakamura, Y.; Ishikawa, H.; Matsuura, A.; Kobayashi, F. Jpn. J. Pharmacol. 1994, 64, 115.

    Article  CAS  PubMed  Google Scholar 

  4. Fujita, M.; Ito, S.; Ota, A.; Kato, N.; Yamamoto, K.; Kawashima, Y.; Yamauchi, H.; Iwao, J. J. Med. Chem. 1990, 33, 1898.

    Article  CAS  PubMed  Google Scholar 

  5. Nazarenko, K. G.; Shtil, N. A.; Chernega, A. N.; Lozinskii, M. O.; Tolmachev, A. A. Synthesis 2004, 1195.

    Article  CAS  Google Scholar 

  6. Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Yoden, T.; Yamagiwa, Y.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Bioorg. Med. Chem. 2000, 8, 393.

    Article  CAS  PubMed  Google Scholar 

  7. Zhang, L. Q.; Guan, L. P.; Wei, C. X.; Deng, X. Q.; Quan, Z. S. Chem. Pharm. Bull. 2010, 58, 326.

    Article  CAS  PubMed  Google Scholar 

  8. Todorov, D. K.; Ilarionova, M. V.; Gupta, R. R.; Molnar, J.; Motohashi, N. Heterocycl. Commun. 1995, 1, 153.

  9. Del Corona, L.; Signorelli, G.; Pinzetta, A.; Coppi, G. Eur. J. Med. Chem. 1992, 27, 419.

    Article  Google Scholar 

  10. Sala, A.; Barani, R.; Benedini, F.; Bertolini, G.; Dona, G.; Gromo, G.; Levi, S. T. US Patent 5480882A, 1996.

  11. Konda, S.; Raparthi, S.; Bhaskar, K.; Munaganti, R. K.; Guguloth, V.; Nagarapu, L.; Akkewar, D. M. Bioorg. Med. Chem. Lett. 2015, 25, 1643.

    Article  CAS  PubMed  Google Scholar 

  12. Ladouceur, G. H.; Bear, B.; Bi, C.; Brittelli, D. R.; Burke, M. J.; Chen, G.; Cook, J.; Dumas, J.; Sibley, R.; Turner, M. R. WO Patent 2004043950.

  13. Aoki, K.; Koseki, J.-I.; Takeda, S.; Aburada, M.; Miyamoto, K.-I. Chem. Pharm. Bull. 2007, 55, 922.

    Article  CAS  PubMed  Google Scholar 

  14. Kolos, N. N.; Tishchenko, A. A.; Orlov, V. D.; Berezkina, T. V.; Shishkina, S. V.; Shishkin, O. V. Сhem. Heterocycl. Compd. 2001, 37, 1289. [Khim. Geterotsikl. Soedin. 2001, 1407.]

  15. Dyachenko, V. I.; Galakhov, M. V.; Kolomiets, A. F.; Fokin, A. V. Chem. Heterocycl. Compd. 1989, 25, 1200. [Khim. Geterotsikl. Soedin. 1989, 1429.]

  16. Kamila, S.; Koh, B.; Khan, O.; Zhang, H.; Biehl, E. R. J. Heterocycl. Chem. 2006, 43, 1641.

    Article  CAS  Google Scholar 

  17. Sharifi, A.; Abaee, M. S.; Rouzgard, M.; Mirzaei, M. Synth. Commun. 2013, 43, 2079.

    Article  CAS  Google Scholar 

  18. Sharifi, A.; Ansari, M.,; Darabi, H. R.; Abaee, M. S. Tetrahedron Lett. 2016, 57, 529.

    Article  CAS  Google Scholar 

  19. Jangir, R.; Gadre, S. R.; Argade, N. P. Synthesis 2015, 2631.

  20. Sharma, P. K.; Kumar, M. Res. Chem. Intermed. 2015, 41, 6141.

    Article  CAS  Google Scholar 

  21. Dabholkar, V. V.; Gavande, R. P. Indian J. Chem., Sect B: Org. Chem. Incl. Med. Chem. 2012, 51, 1173.

    Google Scholar 

  22. Shao, P.-L.; Liao, J.-Y.; Ho, Y.-A.; Zhao, Y. Angew. Chem., Int. Ed. 2014, 53, 5435.

    Article  CAS  Google Scholar 

  23. Nagaraj, M.; Sathiyamoorthy, S.; Boominathan, M.; Muthusubramanian, S.; Bhuvanesh, N. J. Heterocycl. Chem. 2013, 50, 1146.

    CAS  Google Scholar 

  24. Penteado, F.; Vieira, M. M.; Perin, G.; Alves, D.; Jacob, R. G.; Santi, C.; Lenardao, E. J. Green Chem. 2016, 18, 6675.

    Article  CAS  Google Scholar 

  25. Manna, S.; Karmakar, P.; Ali, S. S.; Guria, U. N.; Sarkar, R.; Datta, P.; Mandal, D.; Mahapatra, A. K. New J. Chem. 2018, 42, 4951.

    Article  CAS  Google Scholar 

  26. Bi, B.; Lou, Q.-X.; Ding, Y.-Y.; Chen, S.-W.; Zhang, S.-S.; Hu, W.-H.; Zhao, J.-L. Org. Lett. 2015, 17, 540.

    Article  CAS  PubMed  Google Scholar 

  27. El-Hashash, M. A.; Soliman, A. Y.; Bakeer, H. M.; Mohammed, F. K.; Hassan, H. J. Heterocycl. Chem. 2015, 52, 732.

    Article  CAS  Google Scholar 

  28. El-Sakka, S. S.; Soliman, M. H.; Abdullah, R. S. J. Chem. Sci. 2014, 126, 1883.

    Article  CAS  Google Scholar 

  29. Pan, Y.; Chen, C.; Xu, X.; Zhao, H.; Han, J.; Li, H.; Fan, Q.; Xiao, J. Green Chem. 2018, 20, 403.

    Article  CAS  Google Scholar 

  30. Shi, F.; Tan, W.; Zhang, H.-H.; Li, M.; Ye, Q.; Ma, G.-H.; Tu, S.-J.; Li, G. Adv. Synth. Catal. 2013, 355, 3715.

    Article  CAS  Google Scholar 

  31. Núñez-Rico, J. L.; Vidal-Ferran, A. Org. lett. 2013, 15, 2066.

    Google Scholar 

  32. Rozhkov, S. S.; Ovchinnikov, K. L.; Kolobov, A. V. Russ. Chem. Bull., Int. Ed. 2014, 63, 137. [Izv. Akad. Nauk, Ser. Khim. 2014, 63, 137.]

  33. Kamila, S.; Biehl, E. R. Heterocycles 2006, 68, 1931.

    Article  CAS  Google Scholar 

  34. Kim, Y.; Park, K. J.; Choi, Y. S.; Lee, M.-S.; Park, Y. S. Bull. Korean Chem. Soc. 2013, 34, 2531.

    Article  CAS  Google Scholar 

  35. Bergstrand, H.; Karabelas, K.; Sjo, P. WO Patent WO9813368A1.

  36. Bolotov, V. V.; Kovalenko, S. N.; Kovaleva, S. V.; Stepanenko, V. I Chem. Heterocycl. Compd. 2004, 40, 211. [Khim. Geterotsikl. Soedin. 2004, 249.]

  37. Chupakhin, O. N.; Egorov, I. N.; Rusinov, V. L.; Slepukhin, P. A. Russ. Chem. Bull., Int. Ed. 2010, 59, 991. [Izv. Akad. Nauk, Ser. Khim. 2010, 59, 970.]

  38. Han, Y.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan, W.-C. Tetrahedron Lett. 2010, 51, 2023.

    Article  CAS  Google Scholar 

  39. Aoki, K.; Obata, T.; Yamazaki, Y.; Mori, Y.; Hirokawa, H.; Koseki, J.-I.; Hattori, T.; Niitsu, K.; Takeda, S.; Aburada, M.; Miyamoto, K.-I. Chem. Pharm. Bull. 2007, 55, 255.

    Article  CAS  PubMed  Google Scholar 

  40. Utepova, I. A.; Trestsova, M. A.; Chupakhin, O. N.; Charushin, V. N.; Rempel, A. A. Green Chem. 2015, 17, 4401.

    Article  CAS  Google Scholar 

  41. Azev, Y. A.; Ermakova, O. S.; Berseneva, V. S.; Bakulev, V. A.; Ezhikova, M. A.; Kodess, M. I. Russ. J. Org. Chem. 2017, 53, 90. [Zh. Org. Khim. 2017, 53, 94.]

  42. Chupakhin, O. N.; Sidorov, E. O.; Postovskii, I. Yа. Chem. Heterocycl. Compd. 1975, 11, 1224. [Khim. Geterotsikl. Soedin. 1975, 1433.]

  43. Pelipko, V. V.; Makarenko, S. V.; Berestovitskaya, V. M.; Baichurin, R. I. Chem. Heterocycl. Compd. 2016, 52, 574. [Khim. Geterotsikl. Soedin. 2016, 52, 574.]

  44. Ballini, R.; Gabrielli, S.; Palmieri, A. Synlett 2009, 965.

    Article  CAS  Google Scholar 

  45. Ballini, R.; Palmieri, A.; Talaq, M. A. Adv. Synth. Catal. 2009, 351, 2611.

    Article  CAS  Google Scholar 

  46. Smirnov, A. S.; Pekki, A. I.; Makarenko, S. V.; Berestovitskaya, V. M. Rus. J. Gen. Chem. 2007, 77, 153. [Zh. Obshch. Khim. 2007, 77, 163.]

  47. Berestovitskaya, V. M.; Makarenko, S. V.; Smirnov, A. S.; Gubaidullin, A. T.; Litvinov, I. A.; Pekki, A. I.; Sarkisyan, Z. M. Rus. J. Gen. Chem. 2008, 78, 963. [Zh. Obshch. Khim. 2008, 78, 820.]

  48. Slovetskii, V. I. Russ. Chem. Rev. 1971, 40, 393. [Usp. Khim. 1971, 40, 740.]

    Article  Google Scholar 

  49. Pelipko, V. V.; Makarenko, S. V.; Baichurin, R. I.; Berestovitskaya, V. M.; Kovalenko, K. S. Rus. J. Org. Chem. 2017, 53, 1799. [Zh. Org. Khim. 2017, 53, 1765.]

  50. Yavari, I.; Souri, S.; Sirouspour, M.; Djahaniani, H. Synthesis 2006, 3243.

Download references

Author information

Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, 48 Moyka River Embankment, Saint Petersburg, 191186, Russia

    Vasilii V. Pelipko, Ruslan I. Baichurin, Roman P. Kustin, Alexander P. Vinogradov & Sergey V. Makarenko

Authors
  1. Vasilii V. Pelipko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ruslan I. Baichurin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Roman P. Kustin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alexander P. Vinogradov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sergey V. Makarenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sergey V. Makarenko.

Additional information

A Supplementary information file containing IR spectra of compounds 3а, 4a,b, 6a–d, 7a,b, 10a,b, 1H and 13С NMR spectra of all synthesized compounds, as well as 1Н–1H COSY spectra of compounds 3а, 4b, 6d, 10a,b, 1H–13C HMQC and 1H–13C HMBC spectra of compounds 3a, 4a,b, 6b–d, 7a,b, 10a,b is available at the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(7), 729–735

Electronic supplementary material

ESM 1

(PDF 6275 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pelipko, V.V., Baichurin, R.I., Kustin, R.P. et al. Synthesis of nitromethyl-, N-methylindolyl-, or N-methylindolylnitromethyl-substituted 1,4-benzothiazin(diazin)ones and 3-methyl-1,4-benzoxazinones from alkyl 3-nitroacrylates. Chem Heterocycl Comp 54, 729–735 (2018). https://doi.org/10.1007/s10593-018-2339-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-018-2339-2

Keywords

Search

Navigation