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One-pot synthesis of [4-(tert-butyl)-1H-pyrrol-3-yl](phenyl)methanone from tosylmethyl isocyanide and carbonyl compound

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Chemistry of Heterocyclic Compounds Aims and scope

An efficient one-pot synthetic procedure for [4-(tert-butyl)-1H-pyrrol-3-yl](phenyl)methanone was elaborated using acetophenone and trimethylacetaldehyde in the presence of TosMIC and mild base LiOH·H2O. This method is very economical for the synthesis of pyrrole derivatives and was successfully utilized with good yields.

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References

  1. (a) Sbardella, G.; Mai, A.; Artico, M.; Loddo, R.; Setzu, M. G.; La Colla, P. Bioorg. Med. Chem. Lett. 2004, 14, 1537. (b) Raimondi, M. V.; Cascioferro, S.; Schillaci, D.; Petruso, S. Eur. J. Med. Chem. 2006, 41, 1439. (c) Biava, M.; Porretta, G. C.; Poce, G.; Deidda, D.; Pompei, R.; Tafi, A.; Manetti, F. Bioorg. Med. Chem. 2005, 13, 1221.

  2. Di Santo, R.; Tafi, A.; Costi, R.; Botta, M.; Artico, M.; Corelli, F.; Forte, M.; Caporuscio, F.; Angiolella, L.; Palamara, A. T. J. Med. Chem. 2005, 48, 5140.

    Article  CAS  PubMed  Google Scholar 

  3. Bialer, M.; Yagen, B.; Mechoulam, R.; Becker, Y. J. Med. Chem. 1980, 23, 1144.

    Article  CAS  PubMed  Google Scholar 

  4. (a) Dannhardt, G.; Kiefer, W.; Krämer, G.; Maehrlein, S.; Nowe, U.; Fiebich, B. Eur. J. Med. Chem. 2000, 35, 499. (b) Laufer, S. A.; Augustin, J.; Dannhardt, G.; Kiefer, W. J. Med. Chem. 1994, 37, 1894. (c) Khanna, I. K.; Weier, R. M.; Yu, Y.; Collins, P. W.; Miyashiro, J. M.; Koboldt, C. M.; Veenhuizen, A. W.; Currie, J. L.; Seibert, K.; Isakson, P. C. J. Med. Chem. 1997, 40, 1619.

  5. (a) Wakabayashi, K.-i.; Imai, K.; Miyachi, H.; Hashimoto, Y.; Tanatani, A. Bioorg. Med. Chem. 2008, 16, 6799. (b) Lee, H.; Lee, J.; Shin, Y.; Jung, W.; Kim, J.-H.; Park, K.; Ro, S.; Chung, H.-H.; Koh, J. S. Bioorg. Med. Chem. Lett. 2001, 11, 2963.

  6. Artico, M; Di Santo, R.; Costi, R.; Massa, S.; Retico, A.; Artico, M.; Apuzzo, G.; Simonetti, G.; Strippoli, V. J. Med. Chem. 1995, 38, 4223.

    Article  CAS  PubMed  Google Scholar 

  7. Tafi, A.; Costi, R.; Botta, M.; Di Santo, R.; Corelli, F.; Massa, S.; Ciacci, A.; Manetti, F.; Artico, M. J. Med. Chem. 2002, 45, 2720.

    Article  CAS  PubMed  Google Scholar 

  8. (a) Harrington, P. E.; Tius, M. A. Org. Lett. 1999, 1, 649. (b) Sun, H.; Zhang, H.; Ang, E. L.; Zhao, H. Bioorg. Med. Chem. 2018, 26, 1275. (c) Honey; Thareja, S.; Kumar, M.; Sinha, V. R. Eur. J. Med. Chem. 2012, 53, 76.

  9. Rapoport, H.; Harbuck, J. W. J. Org. Chem. 1971, 36, 853.

    Article  CAS  Google Scholar 

  10. Amarnath, V.; Anthony, D. C.; Amarnath, K.; Valentine, W. M.; Wetterau, L. A.; Graham, D. G. J. Org. Chem. 1991, 56, 6924.

    Article  CAS  Google Scholar 

  11. (a) Knorr, L. Ber. Dtsch. Chem. Ges. 1884, 17, 1635. (b) Knorr, L. Justus Liebigs Ann. Chem. 1886, 236, 290. (c) Cheng, L.; Lightner, D. A. Synthesis 1999, 46. (d) Lavecchia, A.; Costi, R.; Artico, M.; Miele, G.; Novellino, E.; Bergamini, A.; Crespan, E.; Maga, G.; Di Santo, R. ChemMedChem 2006, 1, 1379.

  12. (a) Hantzsch, A. Ber. 1890, 23, 1474. (b) Feist, F. Ber. 1902, 35, 1537. (c) Trautwein, A. W.; Süßmuth, R. D.; Jung, G. Bioorg. Med. Chem. Lett. 1998, 8, 2381. (d) Roomi, M. W.; MacDonald, S. F. Can. J. Chem. 1970, 48, 1689.

  13. (a) Paal, C. Ber. 1885, 18, 367. (b) Knorr, L. Ber. 1885, 18, 299. (c) Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2005, 5277. (d) Rao, H. S. P.; Jothilingam, S.; Scheeren, H. W. Tetrahedron 2004, 60, 1625.

  14. (a) Garabatos-Perera, J. R.; Rotstein, B. H.; Thompson, A. J. Org. Chem. 2007, 72, 7382. (b) The Chemistry of Pyrroles; Jones, R. A.; Bean, G. P., Eds.; Academic Press: London, 1977, p. 525.

  15. Thompson, A.; Butler, R. J.; Grundy, M. N.; Laltoo, A. B. E.; Robertson, K. N.; Cameron, T. S. J. Org. Chem. 2005, 70, 3753.

    Article  CAS  PubMed  Google Scholar 

  16. Van Leusen, A. M.; Hoogenboom, B. E.; Houwing, H. A. J. Org. Chem. 1976, 41, 711.

    Article  CAS  Google Scholar 

  17. Possel, O.; Van Leusen, A. M. Tetrahedron Lett. 1977, 18, 4229.

    Article  Google Scholar 

  18. Oldenziel, O. H.; Van Leusen, A. M. Tetrahedron Lett. 1974, 15, 167.

    Article  Google Scholar 

  19. (a) Kumar, V.; Nair, V. A. Tetrahedron Lett. 2010, 51, 966. (b) Khatik, G. L.; Pal, A.; Mobin, S. M.; Nair, V. A. Tetrahedron Lett. 2010, 51, 3654. (c) Chouhan, M.; Sharma, R.; Nair, V. A. Appl. Organomet. Chem. 2011, 25, 470.

  20. (a) Chouhan, M.; Kumar, K.; Sharma, R.; Grover, V.; Nair, V. A. Tetrahedron Lett. 2013, 54, 4540. (b) Goyal, S.; Patel, J. K.; Gangar, M.; Kumar, K.; Nair, V. A. RSC Adv. 2015, 5, 3187. (c) Kumar, V.; Kumar, K.; Pal, A.; Khatik, G. L.; Nair, V. A. Tetrahedron 2013, 69, 1747. (d) Kumar, K.; Mudshinge, S. R.; Goyal, S.; Gangar, M.; Nair, V. A. Tetrahedron Lett. 2015, 56, 1266. (e) Chouhan, M.; Senwar, K. R.; Kumar, K.; Sharma, R.; Nair, V. A. Synthesis 2014, 195. (f) Sharma, R.; Kumar, K.; Chouhan, M.; Grover, V.; Nair, V. A. RSC Adv. 2013, 3, 14521.

  21. (a) Goyal, S.; Patel, B.; Sharma, R.; Chouhan, M.; Kumar, K.; Gangar, M.; Nair, V. A. Tetrahedron Lett. 2015, 56, 5409. (b) Kumar, K.; More, S. S.; Goyal, S.; Gangar, M.; Khatik, G. L.; Rawal, R. K.; Nair, V. A. Tetrahedron Lett. 2016, 57, 2315. (c) Kumar, K.; Siddique, J.; Gangar, M.; Goyal, S.; Rawal, R. K.; Nair, V. A. ChemistrySelect 2016, 1, 2409. (d) Kumar, K.; Konar, D.; Goyal, S.; Gangar, M.; Chouhan, M.; Rawal, R. K.; Nair, V. A. ChemistrySelect 2016, 1, 3228. (e) Kumar, K.; Konar, D.; Goyal, S.; Gangar, M.; Chouhan, M.; Rawal, R. K.; Nair, V. A. J. Org. Chem. 2016, 81, 9757. (f) Kumar, K.; More, S. S.; Khatik, G. L.; Rawal, R. K.; Nair, V. A. J. Heterocycl. Chem. 2017, 54, 2696. (g) Kaur, R.; Manjal, S. K.; Rawal, R. K.; Kumar, K. Bioorg. Med. Chem. 2017, 25, 4533. (h) Manjal, S. K.; Kaur, R.; Bhatia, R.; Kumar, K.; Singh, V.; Shankar, R.; Kaur, R.; Rawal, R. K. Bioorg. Chem. 2017, 75, 406.

  22. (a) Mittal, M.; Kumar, K.; Anghore, D.; Rawal, R. K. Curr. Drug Discovery Technol. 2017, 14, 106. (b) Kaur, R.; Chaudhary, S.; Kumar, K.; Gupta, M. K.; Rawal, R. K. Eur. J. Med. Chem. 2017, 132, 108. (c) Kumar, B.; Singh, V.; Shankar, R.; Kumar, K.; Rawal, R. K. Curr. Top. Med. Chem. 2017, 17, 148. (d) Talwan, P.; Chaudhary, S.; Kumar, K.; Rawal, R. K. Curr. Bioact. Compd. 2017, 13, 109. (e) Kaur, R.; Rani, V.; Abbot, V.; Kapoor, Y.; Konar, D.; Kumar, K. J. Pharm. Chem. Chem. Sci. 2017, 1, 17.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Indo-Soviet Friendship College of Pharmacy (ISFCP), Moga, Punjab, 142001, India

    Ramandeep Kaur

  2. School of Pharmaceutical Sciences, Apeejay Stya University, Sohna-Palwal Road, Sohna, Gurgaon, Haryana, 122103, India

    Kapil Kumar

  3. National Institute of Pharmaceutical Education and Research, Sector-67, S.A.S. Nagar, Mohali, Punjab, 160062, India

    Kapil Kumar

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  1. Ramandeep Kaur
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  2. Kapil Kumar
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Correspondence to Kapil Kumar.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(7), 700–702

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Kaur, R., Kumar, K. One-pot synthesis of [4-(tert-butyl)-1H-pyrrol-3-yl](phenyl)methanone from tosylmethyl isocyanide and carbonyl compound. Chem Heterocycl Comp 54, 700–702 (2018). https://doi.org/10.1007/s10593-018-2335-6

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  • DOI: https://doi.org/10.1007/s10593-018-2335-6

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