Skip to main content
SpringerLink
Log in

Synthesis of 1'-aryl-3''-(1H-benzotriazol-1-yl)-5',5'',6',6'',7',7a'-hexahydro-1'H,8''H-dispiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine-2',7''-indolizin]-8''-ones via cycloaddition reaction

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The 1,3-dipolar cycloaddition reaction of (E)-7-arylidene-3-(1H-benzotriazol-1-yl)-6,7-dihydroindolizin-8(5H)-one and azomethine ylide which was generated in situ by the reaction of 11H-indeno[1,2-b]quinoxalin-11-one and L-proline afforded novel 1'-aryl-3”-(1H-benzotriazol-1-yl)-5',5”,6',6”,7',7a'-hexahydro-1'H,8”H-dispiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine-2',7”-indolizin]-8”-one in moderate yields. The structures of all the products were characterized thoroughly by NMR, IR spectra, 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.
Scheme 2.

Similar content being viewed by others

References

  1. (a) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863. (b) Tang, S.; Zhang, X.; Sun, J.; Niu, D.; Chruma, J. J. Chem. Rev. 2018, 118, 10393. (c) Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003.

  2. (a) Williams, B. M.; Trauner, D. J. Org. Chem. 2018, 83, 3061. (b) Hauduc, C.; Bélanger, G. J. Org. Chem. 2017, 82, 4703. (c) Men, Y.; Dong, J.; Wang, S.; Xu, X. Org. Lett. 2017, 19, 6712. (d) Lu, X.; Tian, F.; Xu, X.; Wang, N.; Zhang, Q. J. Am. Chem. Soc. 2003, 125, 10459. (e) Maroto, E. E.; Izquierdo, M.; Reboredo, S.; Marco-Martínez, J.; Filippone, S.; Martín, N. Acc. Chem. Res. 2014, 47, 2660. (f) Cho, E.; Shin, S.; Yoon, Y. G. J. Phys. Chem. C 2008, 112, 11667.

  3. (a) Saliyeva, L. M.; Slyvka, N. Y.; Mel'nyk, D. A.; Rusanov, E. B.; Vas'kevich, R. I.; Vovk, M. V. Chem. Heterocycl. Compd. 2018, 54, 130. [Khim. Geterotsikl. Soedin. 2018, 54, 130.] (b) Hu, X.; Huang, Y.; Fu, X.; Li, X. Chem. Heterocycl. Compd. 2019, 55, 644. [Khim. Geterotsikl. Soedin. 2019, 55, 644.] (c) Finke, A. O.; Mironov, M. E.; Skorova, A. B.; Shults, E. E. Chem. Heterocycl. Compd. 2018, 54, 411. [Khim. Geterotsikl. Soedin. 2018, 54, 411.] (d) Korotaev, V. Y.; Kutyashev, I. B.; Barkov, A. Y.; Sosnovskikh, V. Y. Chem. Heterocycl. Compd. 2017, 53, 1192. [Khim. Geterotsikl. Soedin. 2017, 53, 1192.] (e) Ren, D.; Kuang, G.; Li, X. Chem. Heterocycl. Compd. 2018, 54, 1117. [Khim. Geterotsikl. Soedin. 2018, 54, 1117.] (f) Ren, D.; Hu, X.; Li, X. Chem. Heterocycl. Compd. 2019, 55, 275. [Khim. Geterotsikl. Soedin. 2019, 55, 275.]

  4. (a) Filatov, A. S.; Knyazev, N. A.; Ryazantsev, M. N.; Suslonov, V. V.; Larina, A. G.; Molchanov, A. P.; Kostikov, R. R.; Boitsov, V. M.; Stepakov, A. V. Org. Chem. Front. 2018, 5, 595. (b) Alizadeh, A.; Moafi, L. Heterocycl. Commun. 2017, 23, 375. (c) Barkov, A. Y.; Zimnitskiy, N. S.; Kutyashev, I. B.; Korotaev, V. Y.; Sosnovskikh, V. Y. Chem. Heterocycl. Compd. 2018, 54, 43. [Khim. Geterotsikl. Soedin. 2018, 54, 43.] (d) Barkov, A. Y.; Zimnitskiy, N. S.; Kutyashev, I. B.; Korotaev, V. Y.; Sosnovskikh, V. Y. Chem. Heterocycl. Compd. 2017, 53, 1315. [Khim. Geterotsikl. Soedin. 2017, 53, 1315.]

  5. (a) Stępień, M.; Gońka, E.; Żyła, M.; Sprutta, N. Chem. Rev. 2017, 117, 3479. (b) Li, J.; Chen, S.; Wang, Z. Chem. Rec. 2016, 16, 1518.

  6. (a) Tseng, C.-H.; Chen, Y.-R.; Tzeng, C.-C.; Liu, W.; Chou, C.-K.; Chiu, C.-C.; Chen, Y.-L. Eur. J. Med. Chem. 2016, 108, 258. (b) Selvam, P.; Clercq, E. D.; Pannecouque, C. Int. J. Drug Des. Discovery 2013, 4, 1017. (c) Schepetkin, I. A.; Kirpotina, L. N.; Khlebnikov, A. I.; Hanks, T. S.; Kochetkova, I.; Pascual, D. W.; Jutila, M. A.; Quinn, M. T. Mol. Pharmacol. 2012, 81, 832.

  7. Reddy, M. V. R.; Rao, M. R.; Rhodes, D.; Hansen, M. S. T.; Rubins, K.; Bushman, F. D.; Venkateswarlu, Y.; Faulkner, D. J. J. Med. Chem. 1999, 42, 1901.

    Article  CAS  Google Scholar 

  8. De, A. U.; Saha, B. P. J. Pharm. Sci. 1973, 62, 1897.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  10. 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 

  11. 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 

  12. (a) Fu, X.; Meng, Y.; Li, X.; Stepien, M.; Chmielewski, P. J. Chem. Commun. 2018, 54, 2510. (b) Li, X.; Liu, B.; Yu, X.; Yi, P.; Yi, R.; Chmielewski, P. J. J. Org. Chem. 2012, 77, 2431. (c) Yang, L.-L.; Li, X.-F.; Hu, X.-L.; Yu, X.-Y. Tetrahedron Lett. 2016, 57, 1265. (d) Ren, D.; Liu, B.; Li, X.; Koniarz, S.; Pawlicki, M.; Chmielewski, P. J. Org. Chem. Front. 2019, 6, 908. (e) Liu, B.; Li, X.-F.; Liu, H.-C.; Yu, X.-Y. Tetrahedron Lett. 2013, 54, 6952. (f) Ren, D.; Koniarz, S.; Li, X.; Chmielewski, P. J. Chem. Commun. 2020, 56, 4836. (g) Huang, Y.; Tang, G.; Ren, D.; Zeng, J.-L.; Li, X. Chem. Heterocycl. Compd. 2020, 56, 42. [Khim. Geterotsikl. Soedin. 2020, 56, 42.] (h) Huang, Y.; Ren, D.; Yu, X.; Zeng, J.-L.; Li, X. Chem. Heterocycl. Compd. 2020, 56, 84. [Khim. Geterotsikl. Soedin. 2020, 56, 84.]

  13. (a) Raj, A. A.; Raghunathan, R.; SrideviKumari, M. R.; Raman, N. Bioorg. Med. Chem. 2003, 11, 407. (b) Periyasami, G.; Raghunathan, R.; Surendiran, G.; Mathivanan, N. Bioorg. Med. Chem. Lett. 2008, 18, 2342. (c) Kumar, R. R.; Perumal, S.; Manju, S. C.; Bhatt, P.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2009, 19, 3461. (d) Babu, A. R. S.; Raghunathan, R. Tetrahedron Lett. 2008, 49, 4487. (e) Babu, A. R. S.; Raghunathan, R. Tetrahedron Lett. 2007, 48, 6809.

  14. Barkov, A. Y.; Zimnitskiy, N. S.; Korotaev, V. Y.; Kutyashev, I. B.; Moshkin, V. S.; Sosnovskikh, V. Y. Chem. Heterocycl. Compd. 2017, 53, 451. [Khim. Geterotsikl. Soedin. 2017, 53, 451.]

  15. Kumar, R. R.; Perumal, S.; Senthilkumar, P.; Yogeeswari, P.; Sriram, D. Tetrahedron 2008, 64, 2962.

    Article  CAS  Google Scholar 

  16. Huang, Y.; Lei, J.; Fu, X.; Xie, W.; Li, X. J. Chem. Res. 2019, 43, 179.

    Article  CAS  Google Scholar 

  17. (a) APEX2; Bruker-AXS: Madison, 2014. (b) SAINT; Bruker-AXS: Madison, 2014. b Sheldrick, G. M. SADABS; University of Göttingen: Göttingen, 1996. c Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339. d Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

Download references

Author information

Authors and Affiliations

  1. College of Resources and Environment, Zunyi Normal University, Zunyi Pingan Road, Zunyi, 563006, China

    Yulin Ling

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

    Yulin Huang & Xiaofang Li

Authors
  1. Yulin Ling
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yulin Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiaofang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yulin Ling.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(2), 181–186

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ling, Y., Huang, Y. & Li, X. Synthesis of 1'-aryl-3''-(1H-benzotriazol-1-yl)-5',5'',6',6'',7',7a'-hexahydro-1'H,8''H-dispiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizine-2',7''-indolizin]-8''-ones via cycloaddition reaction. Chem Heterocycl Comp 57, 181–186 (2021). https://doi.org/10.1007/s10593-021-02891-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-02891-w

Keywords

Search

Navigation