Skip to main content
SpringerLink
Log in

Synthesis of symmetrical chromeno[2,3-b]chromenes on the basis of о-quinone methides and 1,1-bis(morpholino)ethene

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 1,1-bis(morpholino)ethene with precursors of о-quinone methides derived from Mannich bases of phenols and 2-naphthols provided a series of chromeno[2,3-b]chromenes. The cascade process included a hetero-Diels–Alder reaction between о-quinone methide and ketenaminal, elimination of secondary amine, and [4+2] cycloaddition between о-quinone methide and the chromene intermediate.

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.

Figure 1.
Figure 2.

Similar content being viewed by others

References

  1. (a) Kantlehner, W. In Science of Synthesis; de Meijere, A., Ed.; Thieme: Stuttgart, 2006, Vol. 24, p. 571. (b) Keller, P. A.; Morgan, J. In Science of Synthesis; de Meijere, A., Ed.; Thieme: Stuttgart, 2006, Vol. 24, p. 707. (c) Wang, K.-M.; Yan, S.-J.; Lin, J. Eur. J. Org. Chem. 2014, 1129. (d) Huang, Z.-T.; Wang, M.-X. Heterocycles 1994, 37, 1233. (e) Yang, P. H. Res. Chem. Intermed. 2016, 42, 5617.

  2. Rossi, E.; Pini, E. Tetrahedron 1996, 52, 7939.

    Article  CAS  Google Scholar 

  3. Pocar, D.; Rossi, L. M.; Stradi, R. Synthesis 1976, 684.

  4. Fioravanti, S.; Loreto, M. A.; Pellacani, L.; Tardella, P. A. Heterocycles 1987, 25, 433.

    Article  CAS  Google Scholar 

  5. Rajagopalan, P.; Talaty, C. N. Tetrahedron Lett. 1966, 7, 4537.

    Article  Google Scholar 

  6. Haider, N. Tetrahedron 1991, 47, 3959.

    Article  CAS  Google Scholar 

  7. Ficini, J.; Besseyre, J.; Krief, A. Bull. Soc. Chim. Fr. 1976, 987.

  8. von Strandtmann, M.; Cohen, M. P.; Shavel, J., Jr. US Patent 3752830; Chem. Abstr. 1973, 79, 92193.

    Google Scholar 

  9. (a) Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Russ. Chem. Rev. 2017, 86, 625. [Usp. Khim. 2017, 86, 625.] (b) Škalamera, Đ.; Šumanovac Ramljak, T.; Husak, A. Kem. Ind. 2017, 66, 353. (c) Škalamera, Đ.; Husak, A.; Šumanovac Ramljak, T. Kem. Ind. 2017, 66, 481.

  10. Devakaram, R.; Black, D. StC.; Choomuenwai, V.; Davis, R. A.; Kumar, N. Bioorg. Med. Chem. 2012, 20, 1527.

  11. (a) Tan, H.; Wang, G.; Li, J.; Meng, G.; Liu, Z.; Dong, M.; Li, Y.; Ju, D.; Zhang, Q. Bioorg. Med. Chem. 2015, 23, 118. (b) Tan, Y.-X.; Liu, C.; Zhang, T.; Chen, R.-Y.; Yu, D.-Q. Phytochem. Lett. 2010, 3, 57.

  12. Shi, Y. US Patent 20080287526A1.

  13. Li, S.; Shen, C.; Guo, W.; Zhang, X.; Liu, S.; Liang, F.; Xu, Z.; Pei, Z.; Song, H.; Qiu, L.; Lin, Y.; Pang, J. Mar. Drugs 2013, 11, 5159.

    Article  CAS  Google Scholar 

  14. (a) Kimura, Y.; Okuda, H.; Nomura, T.; Fukai, T.; Arichi, S. Chem. Pharm. Bull. 1986, 34, 1223. (b) Qin, J.; Fan, M.; He, J.; Wu, X.-D.; Peng, L.-Y.; Su, J.; Cheng, X.; Li, Y.; Kong, L.-M.; Li, R.-T.; Zhao, Q.-S. Nat. Prod. Res. 2015, 29, 1711. (c) Wang, M.; Gao, L.-X., Wang, J.; Li, J.-Y.; Yu, M.-H.; Li, J.; Hou, A.-J. Phytochemistry 2015, 109, 140. (d) Salae, A.-W.; Chairerk, O.; Sukkoet, P.; Chairat, T.; Prawat, U.; Tuntiwachwuttikul, P; Chalermglin, P.; Ruchirawat, S. Phytochemistry 2017, 135, 135.

  15. Balasubramanian, K. K.; Selvaraj, S. J. Org. Chem. 1980, 45, 3726.

    Article  CAS  Google Scholar 

  16. Osyanin, V. A.; Osipov, D. V.; Borisov, D. D.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2013, 49, 683. [Khim. Geterotsikl. Soedin. 2013, 732.]

  17. Baganz, H.; Domaschke, L. Chem. Ber. 1962, 95, 2095.

    Article  CAS  Google Scholar 

  18. Goldschmidt, Z.; Levinger, S.; Gottlieb, H. Tetrahedron Lett. 1994, 35, 7273.

    Article  CAS  Google Scholar 

  19. (a) Taillefumier, C.; Chapleur, Y. Can. J. Chem. 2000, 78, 708. (b) Messana, I.; Ferrari, F.; Monache, F. D.; Yunes, R. A.; Calixto, J. B.; Bisognin, T. Heterocycles 1991, 32, 1287.

  20. Kirby, A. J.; Martin, R. J. J. Chem. Soc., Perkin Trans. 2 1983, 1627.

  21. (a) Siu, A. F. M.; Lambrecht, R. M.; Shani, J.; Pyne, S. G.; Kane-Maguire, L. A. P. J. Labelled Compd. Radiopharm. 1997, 39, 711. (b) Poirier, V.; Roisnel, T.; Carpentier, J.-F.; Sarazin, Y. Dalton Trans. 2011, 40, 523. (c) Tian, J.; Zhang, J.; Shen, X.; Zou, H. J. Organomet. Chem. 1999, 584, 240. (d) Mahato, S.; Haldar, S.; Jana, C. K. Chem. Commun. 2014, 50, 332.

  22. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71, 3.

Download references

This work received financial support from the Ministry of Education and Science of the Russian Federation (contract 02.a03.21.0008), the Russian Foundation for Basic Research, and the Samara Regional Government within the framework of the scientific project 17-43-630838 r_a.

Author information

Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeiskaya St., Samara, 443100, Russia

    Vitaly A. Osyanin, Dmitry V. Osipov, Maxim R. Demidov, Pavel E. Krasnikov & Yuri N. Klimochkin

  2. RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Vitaly A. Osyanin

Authors
  1. Vitaly A. Osyanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dmitry V. Osipov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Maxim R. Demidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pavel E. Krasnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yuri N. Klimochkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vitaly A. Osyanin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(12), 1310–1314

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Osyanin, V.A., Osipov, D.V., Demidov, M.R. et al. Synthesis of symmetrical chromeno[2,3-b]chromenes on the basis of о-quinone methides and 1,1-bis(morpholino)ethene. Chem Heterocycl Comp 53, 1310–1314 (2017). https://doi.org/10.1007/s10593-018-2211-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-018-2211-4

Keywords

Search

Navigation