Skip to main content
Log in

Synergic Synthesis and Characterization of tert-Butyl 4-[(E)-But-1-en-3-yn-1-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

tert-Butyl 4-[(E)-but-1-en-3-yn-1-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate has been synthesized with a good yield and selectivity starting from commercially available 4-bromo-1H-indole and using simple reagents. The title compound is a potential precursor to biologically active natural products like Indiacen A and Indiacen B. The newly synthesized compounds were characterized by spectral data.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1.
Scheme

Similar content being viewed by others

REFERENCES

  1. Nguyen, T.T., Koh, M.H., Mann, T.J., Schrock, R.R., and Hoveyda, A.H., Nature, 2017, vol. 552, p. 347. https://doi.org/10.1038/nature25002

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Marsch, N., Kock, M., and Lindel, T., Beilstein J. Org. Chem., 2016, vol. 12, p. 334. https://doi.org/10.3762/bjoc.12.36

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Steinmetz, H., Mohr, K.I., Zander, W., Jansen, R., Gerth, K., and Müller, R., J. Nat. Prod., 2012, vol. 75, p. 1803. https://doi.org/10.1021/np300288b

    Article  CAS  PubMed  Google Scholar 

  4. Anantoju, K.K., Mohd, B.S., and Maringanti, T.C., Tetrahedron Lett., 2017, vol. 58, no. 15, p. 1499. https://doi.org/10.1016/j.tetlet.2017.03.002

    Article  CAS  Google Scholar 

  5. Shaikh, T.M.A. and Debebe, H., J. Chem., 2020, vol. 9, article ID 4358453. https://doi.org/10.1155/2020/4358453

  6. Adam, J.M., Cairns, J., Caulfield, W., Cowley, P., Cumming, I., Easson, M., Edwards, D., Ferguson, M., Goodwin, R., Jeremiah, F., Kiyoi, T., Mistry, A., Moir, E., Morphy, R., Tierney, J., York, M., Baker, J., Cottney, J., Houghton, A., Westwood, P., and Walker, G., MedChemComm, 2010, vol. 1, p. 54. https://doi.org/10.1039/C0MD00022A

    Article  CAS  Google Scholar 

  7. Choppara, P., Prasad, Y.V., Rao, C.V., Hari Krishna, K., Trimoorthulu, G., Maheswara Rao, G.U., Venkateswara Rao, J., Bethu, M.S, and Murthy, Y.L.N., Arab. J. Chem., 2019, vol. 12, no. 8, p. 2328. https://doi.org/10.1016/j.arabjc.2015.02.006

    Article  CAS  Google Scholar 

  8. Lauchli, R. and Shea, K.J., Org. Lett., 2006, vol. 8, p. 5287. https://doi.org/10.1021/ol0620747

    Article  CAS  PubMed  Google Scholar 

  9. Madadi, N.R., Penthala, N.R., Janganati, V., and Crooks, P.A., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 601. https://doi.org/10.1016/j.bmcl.2013.12.013

    Article  CAS  PubMed  Google Scholar 

  10. Singh, P., Mittal, A., Bhardwaj, A., Kaur, S., and Kumar, S., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 85. https://doi.org/10.1016/j.bmcl.2007.11.010

    Article  CAS  PubMed  Google Scholar 

  11. Mashayekhi, V., Tehrani, K.H.M.E., Azerang, P., Sardari, S., and Kobarfard, F., Arch. Pharmacal Res., 2021, vol. 44. p. 1. https://doi.org/10.1007/s12272-013-0242-z

    Article  CAS  Google Scholar 

  12. Hall, A., Billinton, A., Brown, S.H., Chowdhury, A., Giblin, G.M.P., Goldsmith, P., Hurst, D.N., Naylor, A., Patel, S., and Scoccitti, T., Bioorg. Med. Chem. Lett., 2008, vol. 18. p. 2684. https://doi.org/10.1016/j.bmcl.2008.03.018

    Article  CAS  PubMed  Google Scholar 

  13. Moir, E.M., Yoshiizumi, K., Cairns, J., Cowley, P., Ferguson, M., Jeremiah, F., Kiyoi, T., Morphy, R., Tierney, J., Wishart, G., York, M., Baker, J., Cottney, J.E., Houghton, A.K., McPhail, P., Osprey, A., Walker, G., and Adam, J.A., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 7327. https://doi.org/10.1016/j.bmcl.2010.10.061

    Article  CAS  PubMed  Google Scholar 

  14. Madadi, N.R., Penthala, N.R., Brents, L.K., Ford, B.M., Prather, P.L., and Crooks, P.A., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 2019. https://doi.org/10.1016/j.bmcl.2013.02.025

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Ryoichi, K. and Manabu, K., Org. Lett., 2006, vol. 8, no. 12, p. 2653. https://doi.org/10.1021/ol061039x

    Article  CAS  Google Scholar 

  16. Badenock, J.C., Jordan, J.A., and Gribble, G.W., Tetra­hedron Lett., 2013, vol. 54, nol. 22, p. 2759. https://doi.org/10.1016/j.tetlet.2013.02.116

    Article  CAS  Google Scholar 

  17. Moyer, M.P., Shiurba, J.F., and Rapoport, H., J. Org. Chem., 1986, vol. 51, p. 5106. https://doi.org/10.1021/jo00376a010

    Article  CAS  Google Scholar 

  18. Netz, N. and Opatz, T., J. Org. Chem., 2016, vol. 81, p. 1723. https://doi.org/10.1021/acs.joc.5b02815

    Article  CAS  PubMed  Google Scholar 

  19. Gibson, A.W., Humphrey, G.R., Kennedy, D.J., and Wright, S.H.B., Synthesis, 1991, vol. 1991, no. 5, p. 414. https://doi.org/10.1055/s-1991-26481

    Article  Google Scholar 

  20. Burke, L.T., Dixon, D.J., Ley, S.V., and Rodríguez, F., Org. Lett., 2000, vol. 2, p. 3611. https://doi.org/10.1021/ol006493u

    Article  CAS  PubMed  Google Scholar 

  21. Wang, Y., Huang, B., Bin, H., Sheng, Sh., and Cai, M., J. Chem Res., 2007, no. 12, p. 728. https://doi.org/10.3184/030823407X275928

    Article  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are thankful to Management and Principal, Sreenidhi Institute of Science and Technology, Hyderabad, India for providing necessary facilities to carry out this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. Laxminarayana.

Ethics declarations

The authors declare the absence of conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kumar, B.R., Kumar, A.K., Reddy, B.S. et al. Synergic Synthesis and Characterization of tert-Butyl 4-[(E)-But-1-en-3-yn-1-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate. Russ J Org Chem 58, 580–583 (2022). https://doi.org/10.1134/S1070428022040169

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022040169

Keywords:

Navigation