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Bu3P-mediated acylation of (E)-7-arylidene-6,7-dihydroindolizin-8(5H)-ones with acyl chlorides

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Chemistry of Heterocyclic Compounds Aims and scope

The (Z)-7-(1,2-diaryl-2-oxoethylidene)-6,7-dihydroindolizin-8(5H)-ones were synthesized in the acylation reaction of (E)-7-arylidene-6,7-dihydroindolizin-8(5H)-ones with acyl chlorides in the presence of Bu3P in moderate yields. The structures of all products were characterized thoroughly by NMR, IR, HRMS together with X-ray crystallographic analysis.

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References

  1. (a)Guo, H.; Fan, Y. C.; Sun, Z.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049. (b) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535. (c) Xu, S.; He, Z. RSC Adv. 2013, 3, 16885. (d) Karanam, P.; Reddy, G. M.; Koppolu, S. R.; Lin, W. Tetrahedron Lett. 2018, 59, 59.

  2. Das, U.; Tsai,Y.-L.; Y.; Lin, W. Org. Biomol. Chem. 2014, 12, 4044.

  3. Kao, T.-T.; Syu, S.; Lin, W. Org. Lett. 2010, 12, 3066.

    Article  CAS  Google Scholar 

  4. Chen, K.-W.; Syu, S.; Jang, Y.-J.; Lin, W. Org. Biomol. Chem. 2011, 9, 2098.

    Article  CAS  Google Scholar 

  5. Syu, S.; Lee, Y.-T.; Jang, Y.-J.; Lin, W. Org. Lett. 2011, 13, 2970.

    Article  CAS  Google Scholar 

  6. Jang, Y.-J.; Syu, S.; Chen, Y.-J.; Yang, M.-C.; Lin, W. Org. Biomol. Chem. 2012, 10, 843.

    Article  CAS  Google Scholar 

  7. Tsai, Y.-L.; Das, U.; Syu, S.; Lee, C.-J.; Lin, W. Eur. J. Org. Chem. 2013, 4634.

  8. (a) Zhang, S.; Greenhalgh, M. D.; Slawin, A. M. Z.; Smith, A. D. Chem. Sci. 2020, 11, 3885. (b) Yang, B.; Huang, Z.; Guan, H.; Niu, X.; Li, Y.; Fang, S.; Ma, C. Tetrahedron Lett. 2013, 54, 5994. (c) Michael, J. P. Nat. Prod. Rep. 2008, 25, 139. (d) Amos, R. I. J.; Gourlay, B. S.; Molesworth, P. P.; Smith, J. A.; Sprod, O. R. Tetrahedron 2005, 61, 8226. (e) Dinsmore, A.; Mandy, K.; Michael, J. P. Org. Biomol. Chem. 2006, 4, 1032. (f) Barton, D. H. R.; Pereira, M. M. M. A.; Taylor, D. K. Tetrahedron Lett. 1994, 35, 9157.

  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. 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 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. 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 

  14. (a) Huang, Y.; Tang, G.; Ren, D.; Zeng, J.-L.; Li, X. Chem. Heterocycl. Compd. 2020, 56, 42. [Khim. Geterotsikl. Soedin. 2020, 56, 42.] (b) Li, Y.; Tang, J.; Li, X. Chem. Heterocycl. Compd. 2020, 56, 1062. [Khim. Geterotsikl. Soedin. 2020, 56, 1062.] (c) Ren, D.; Hu, X.; Li, X. Chem. Heterocycl. Compd. 2019, 55, 275. [Khim. Geterotsikl. Soedin. 2019, 55, 275.] (d) Huang, Y.; Lei, J.; Fu, X.; Xie, W.; Li, X. J. Chem. Res. 2019, 43, 179. b Zhang, S.; Hu, X.; Tao, H.; Liu, H.; Li, X. J. Chem. Res. 2017, 41, 608.

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

    Article  Google Scholar 

  16. (a) APEX2, SADABS, SAINT, SHELXTL, XCIF, XPREP; Bruker AXS, Inc.: Madison, 2014. (b) Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339. (c) Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

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This research was supported by National Natural Science Foundation of China (No. 21671063).

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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, Taoyuan Road, Xiangtan, 411201, Hunan, China

    Sha Li, Jiaxi Tan & Xiaofang Li

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  1. Sha Li
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  2. Jiaxi Tan
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  3. Xiaofang Li
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Correspondence to Xiaofang Li.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(5), 538–542

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Li, S., Tan, J. & Li, X. Bu3P-mediated acylation of (E)-7-arylidene-6,7-dihydroindolizin-8(5H)-ones with acyl chlorides. Chem Heterocycl Comp 57, 538–542 (2021). https://doi.org/10.1007/s10593-021-02939-x

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  • DOI: https://doi.org/10.1007/s10593-021-02939-x

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