Skip to main content
SpringerLink
Log in

Synthesis of novel 2'-aryl-4'-hydroxy-4',5,5',6-tetrahydro- 2'H,8H-spiro[indolizine-7,3'-thiophen]-8-one derivatives via sulfa-Michael/aldol cascade reactions

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The sulfa-Michael/aldol cascade reaction of (E)-7-arylidene-6,7-dihydroindolizin-8(5H)-ones and 1,4-dithiane-2,5-diol afforded novel 2'-aryl-4'-hydroxy-4',5,5',6-tetrahydro-2'H,8H-spiro[indolizine-7,3'-thiophen]-8-ones in low to moderate yields. The structures of all products were characterized thoroughly by NMR, IR, HRMS, together with X-ray crystallographic analysis.

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

Scheme 1.
Figure 1.
Figure 2.
Figure 3.

Similar content being viewed by others

References

  1. Michael, J. P. Nat. Prod. Rep.2007, 24, 191.

    Article  CAS  Google Scholar 

  2. Dinsmore, A.; Mandy, K.; Michael, J. P. Org. Biomol. Chem.2006, 4, 1032.

    Article  CAS  Google Scholar 

  3. Amos, R. I. J.; Gourlay, B. S.; Molesworth, P. P.; Smith, J. A.; Sprod, O. R. Tetrahedron2005, 61, 8226.

    Article  CAS  Google Scholar 

  4. Toyooka, N.; Zhou, D.; Nemoto, H. J. Org. Chem.2008, 73, 4575.

    Article  CAS  Google Scholar 

  5. (a) Wang, J.-J.; Feng, X.; Xun, Z.; Shi, D.-Q.; Huang, Z.-B. J. Org. Chem.2015, 80, 8435. (b) Cui, P.; Xu, L.; Shi, Z.; Gan, L. J. Org. Chem.2011, 76, 4210. (c) Liu, B.; Li, X.; Zhang, J.; Du, L.; Zeng, R. J. Chem. Res.2013, 37, 681. (d) Ren, D.; Lei, J.; Yu, X.; Huang, Y.; Li, X. J. Chem. Res.2018, 42, 628. (e) Li, X.; Yi, R.; Liu, B.; Li, Z.; Yu, X.; Yi, P. Chin. J. Org. Chem.2012, 32, 2309. (f) Zhang, S.; Hu, X.; Tao, H.; Liu, H.; Li, X. J. Chem. Res.2017, 41, 608. (g) Angle, S. R.; Qian, X. L.; Pletnev, A. A.; Chinn, J. J. Org. Chem.2007, 72, 2015.

  6. Wan, Y.; Dai, N.; Tang, Z.; Fang, H. Eur. J. Med. Chem. 2018, 146, 471.

    Article  CAS  Google Scholar 

  7. De, A. U.; Saha, B. P. J. Pharm. Sci.1973, 62, 1363.

    Article  CAS  Google Scholar 

  8. James, D. A.; Koya, K.; Li, H.; Chen, S.; Xia, Z.; Ying, W.; Wu, Y.; Sun, L. Bioorg. Med. Chem. Lett.2006, 16, 5164.

    Article  CAS  Google Scholar 

  9. La Pietra, V.; La Regina, G.; Coluccia, A.; Famiglini, V.; Pelliccia, S.; Plotkin, B.; Eldar-Finkelman, H.; Brancale, A.; Ballatore, C.; Crowe, A.; Brunden, K. R.; Marinelli, L.; Novellino, E.; Silvestri, R. J. Med. Chem.2013, 56, 10066.

    Article  Google Scholar 

  10. Haraguchi, K.; Shimada, H.; Tanaka, H.; Hamasaki, T.; Baba, M.; Gullen, E. A.; Dutschman, G. E.; Cheng, Y.-C. J. Med. Chem.2008, 51, 1885.

    Article  CAS  Google Scholar 

  11. Volkmann, R. A.; Kelbaugh, P. R.; Nason, D. M.; Jasys, V. J. J. Org. Chem.1992, 57, 4352.

    Article  CAS  Google Scholar 

  12. Yoshikawa, M.; Morikawa, T.; Matsuda, H.; Tanabe, G.; Muraoka, O. Bioorg. Med. Chem.2002, 10, 1547.

    Article  CAS  Google Scholar 

  13. Jeong, L. S.; Choe, S. A.; Gunaga, P.; Kim, H. O.; Lee, H. W.; Lee, S. K.; Tosh, D. K.; Patel, A.; Palaniappan, K. K.; Gao, Z.-G.; Jacobson, K. A.; Moon, H. R. J. Med. Chem.2007, 50, 3159.

    Article  CAS  Google Scholar 

  14. Qiao, C.; Ling, K. Q.; Shepard, E. M.; Dooley D. M.; Sayre, L. M. J. Am. Chem. Soc.2006, 128, 6206.

    Article  CAS  Google Scholar 

  15. (a) Chauhan, P.; Mahajan, S.; Enders, D. Chem. Rev.2014, 114, 8807. (b) Duan, S.-W.; Li, Y.; Liu, Y.-Y.; Zou, Y.-Q.; Shi, D.-Q.; Xiao, W.-J. Chem. Commun. 2012, 48, 5160. (c) Kowalczyk, D.; Wojciechowski, J.; Albrecht, L. Tetrahedron Lett.2016, 57, 2533. (d) Kumara, C. S. P.; Gowda, G. B.; Kumar, K. S. V.; Ramesh, N.; Sadashiva, M. P.; Junjappa, H. Tetrahedron Lett.2016, 57, 4302. (e) Zhang, S.; Ren, D.; Hu, X.; Fu, X.; Li, X. J. Chem. Res.2017, 41, 641. (f) Yan, J.; Fu, X.; Li, W. J. Chem. Res.2017, 41, 722. (g) De Risi, C.; Benetti, S.; Fogagnolo, M.; Bertolasi, V. Tetrahedron Lett.2013, 54, 283. (h) Nagaraju, S.; Sathish, K.; Paplal, B.; Kashinath, D. Tetrahedron Lett.2017, 58 , 2865.

  16. (a) Ren, D.; Kuo, G.; Li, X. Chem. Heterocycl. Compd.2018, 54, 1117. [Khim. Geterotsikl. Soedin.2018, 54, 1117.] (b) Ren, D.; Hu, X.; Li, X. Chem. Heterocycl. Compd.2019, 55, 275. [Khim. Geterotsikl. Soedin.2019, 55, 275.] (c) Hu, X.; Huang, Y.; Fu, X.; Li, X. Chem. Heterocycl. Compd.2019, 55, 644. [Khim. Geterotsikl. Soedin.2019, 55, 644.] (d) Ren, D.; Liu, B.; Li, X.; Koniarz, S.; Pawlicki, M.; Chmielewski, P. J. Org. Chem. Front. 2019, 6, 908. b Fu, X.; Meng, Y.; Li, X.; Stepien, M.; Chmielewski, P. J. Chem. Commun. 2018, 54, 2510. c Ren, D.; Fu, X.; Li, X.; Koniarz, S.; Chmielewski, P. J. Org. Chem. Front. 2019, 6, 2924

  17. Liu, B.; Li, X.; Zhang, J.; Du, L.; Zeng, R. J. Chem. Res. 2013, 37, 681.

    Article  Google Scholar 

  18. Sheldrick, G. M. SADABS; University of Göttingen, 1996.

  19. Sheldrick, G. M. Acta Crystallogr, Sect. A: Found. Adv.2015, A71, 3.

  20. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschman, H. J. Appl. Crystallogr.2009, 42, 339.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key Laboratory of Theoretical Organic Chemistry and Functional Molecules, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, 411201, Hunan, China

    Yulin Huang, Guihua Tang, Demin Ren & Xiaofang Li

  2. School of Chemistry and Food Engineering, Changsha University of Science and Technology, Changsha, 410114, China

    Ju-Lan Zeng

Authors
  1. Yulin Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Guihua Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Demin Ren
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ju-Lan Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xiaofang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Ju-Lan Zeng or Xiaofang Li.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 42–46

Electronic supplementary material

ESM 1

(PDF 843 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Huang, Y., Tang, G., Ren, D. et al. Synthesis of novel 2'-aryl-4'-hydroxy-4',5,5',6-tetrahydro- 2'H,8H-spiro[indolizine-7,3'-thiophen]-8-one derivatives via sulfa-Michael/aldol cascade reactions. Chem Heterocycl Comp 56, 42–46 (2020). https://doi.org/10.1007/s10593-020-02620-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02620-9

Keywords

Search

Navigation