Document Type: Review Article

Authors

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

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

Abstract

An efficient procedure was developed for the synthesis of different derivatives of 3,4-disubstituted pyrrole using TosMIC with ethyl cinnamate in DMF using lithium hydroxide monohydrate as a base. Further, trisubstituted pyrrole was synthesized using nitrostyrene, ethyl-propiolate and benzylamine in toluene as a reaction medium. This reaction was catalysed by lewis acid FeCl3. This strategy was further modified to synthesized tetra and penta substituted pyrrole using ethanol as a reaction medium keeping other conditions intact. This method is very economical and was successfully utilized for the synthesis of its derivatives with moderate to good yields.

Graphical Abstract

Keywords

Main Subjects

References

  1. (a) G. Sbardella, A. Mai, M. Artico, R. Loddo, M. G. Setzuc, P. L. Collac, Bioorg. Med. Chem. Lett. 2004, 14, 1537; (b) M. V. Raimondi, S. Cascioferro, D. Schillaci, S. Petruso, Eur. J. Med. Chem. 2006, 41, 1439; (c) M. Biava, G. C. Porretta, G. Poce, D. Deidda, R. Pompei, A. Tafi, F. Manetti, Bioorg. Med. Chem. 2005, 13, 1221.
  2. R. Di. Santo, A. Tafi, R. Costi, M. Botta, M. Artico, F. Corelli, M. Forte, F. Caporuscio, L. Angiolella, A. T. Palamara, J. Med. Chem. 2005, 48, 5140.
  3. M. Bialer, B. Yagen, R. Mechoulam, Y. Becker, J. Med. Chem. 1980, 23, 1144.
  4. (a) G. Dannhardt, W. Kiefer, G. Krämer, S. Maehrlein, U. Nowe, B. Fiebich, Eur. J. Med. Chem. 2000, 35, 499; (b) S. Laufer, J. Augustin, G. Dannhardt, W. Kiefer, J. Med. Chem. 1994, 37, 1894; (c) I. K. Khanna, R. M. Weier, P. W. Collins, J. M. Miyashiro, C. M. Koboldt, A. W. Veenhuizen, J. L. Currie, K. Seibert, P. C. Isakson, J. Med. Chem. 1997, 40, 1619.
  5. (a) K. Wakabayashi, K. Imai, H. Miyachi, Y. Hashimoto, A. Tanatani, Bioorg. Med. Chem. 2008, 16, 6799; (b) H. Lee, J. Lee, Y. Shin, W. Jung, J. H. Kim, K. Park, S. Ro, H. H. Chung, J. S. Koh, Bioorg. Med. Chem. Lett. 2001, 11, 2963.
  6. H. Rapoport, J. Harbuck, J. Org. Chem.1971, 36, 853-858.
  7. V. Amarnath, D.  C. Anthony, K. Amarnath, W. M. Valentine, L. A. Wetterau, D. G. Graham, J. Org. Chem. 1991, 56,  6924-6928.
  8. M. Artico, R. D. Santo, R. Costi, S. Massa, A. Retico, M. Artico, G. Apuzzo, G. Simonetti, V. Strippoli, J. Med. Chem.  1996, 38, 4223-4233.
  9. A. Tafi, R. Costi, M. Botta, R. D. Santo, F. Corelli, S. Massa, A. Ciacci, F. Manetti, M. Artico, J. Med. Chem.  2002, 45, 2720-2732.

10. R. D. Santo, A. Tafi, A. Costi, M. Botta, M. Artico, F. Corelli, M. Forte, F. Caporuscio, L. Angiolella, A. T. Palamara, J. Med. Chem. 2005, 48, 5140- 51. 

11. P. E. Harrington, M. A. Tius, Org. Lett. 1999, 1, 649-653.

12. (a) L. Knorr, Ber. 1884, 17, 1635; (b) L. Knorr, Ann. 1886, 236, 290; (c) P. E. Harrington, M. A. Tius, Org. Lett. 1999, 1, 649; (d) L. Cheng, D. A. Lightner, Synthesis 1999, 46; (e) H. Rapoport, J. J. Harbuck, Org. Chem. 1971, 36, 853.

13. (a) A. Hantzsch, Ber. 1890, 23, 1474; (b) F. Feist, Ber. 1902, 35, 1538; (c) A. W. Trautwein, R. D. Submuth, G. Jung, Bioorg. Med. Chem. Lett. 1998, 8, 2381; (d) M. W. Roomi, S. F. MacDonald, Can. J. Chem. 1970, 48, 1689.

14. (a) C. Paal, Ber. 1885, 18, 367; (b) L. Knorr, Ber. 1885, 18, 299; (c) G. Minetto, L. F. Raveglia, A. Sega, M. Taddei, Eur. J. Org. Chem. 2005, 70, 5277; (d) H. S. P. Rao, S. Jothilingam, H. W. Scheeren, Tetrahedron 2004, 60, 1625; (e) V. Amarnath, D. C. Anthony, K. Amarnath, W. M. Valentine, L. A. Wetterau, D. G. Graham, J. Org. Chem. 1991, 56: 6924.

15. (a) S. Maiti, S. Biswas, U. Jana, J. Org. Chem. 2010, 75, 1674; (b) S. Sarkar, K. Bera, S. Maiti, S. Biswas, U. Jana, Synth. Commun. 2013, 43, 1563; (c) L. Li, M. N. Zhao, Z. H Ren, J. Li, Z. H. Guan, Synthesis 2012, 532.

16. V. Est´evez, M. Villacampa, J. C. Men´ endez, Chem. Commun. 2013, 49, 591.

17. (a) H. M. Meshram, B. M. Babu, G. S. Kumar, P. B. Thakur, V. M. Bangade, Tetrahedron Lett. 2013, 54, 2296; (b) I. Adam, H. Yu-Lai, Y. Cai-Xia, J. Med. Chem. Sci., 2019, 2(3), 76-79; (c) I. Amini, S. Mohammadi-Aghdam, F. Divsar, J. Med. Chem. Sci., 2018, 1(2), 26-27; (e) M, Eldefrawy, E. G. A. Gomaa, S. Salem, F. A. Razik, Prog. Chem.  Biochem. Res., 2018, 1(1), 11-18.

18. (a) A. T. Khan, , M. Lal, P. R. Bagdi, R. S. Basha, P. Saravanan, S. Patra, Tetrahedron Lett. 2012, 53, 4145; (b) A.U. Itodo, O. M. Itodo, E. Iornumbe, M. O. Fayomi,  Prog. Chem.  Biochem. Res., 2018, 1(1), 50-59.   

19. C. C. Silveira, S. R. Mendes, G. M. Martins, S. C. Schlösser, T. S. Kaufman, Tetrahedron 2013, 69, 9076.

20. G. R. Reddy, T. R. Reddy, S. C. Joseph, K. S. Reddy, C. L. T. Meda, A. Kandale, D. Rambabu, G. R. Krishna, C. Malla Reddy, K. V. L. Parsa, M. Pal, RSC Adv. 2012, 2, 9142.

21. G. F. Smith, Adv. Heterocycl. Chem. 1963, 2, 287.

22. A. M. Van Leusen, B. E. Hoogenboom, H. A. Houuling, J. Org. Chem. 1976, 41, 711-715.

23. O. Possel, A. M. Van Leusen, Tetrahedron  Lett. 1977, 18,4229-4234.

24. O. H. Oldenziel, A. M. Van Leusen, Tetrahedron  Lett. 1974, 15, 167-170.

25. (a) M. Chouhan, K. Kumar, R. Sharma, V. Grover, V. A. Nair, Tetrahedron Lett. 2013, 54, 4540-4543; (b) S. Goyal, J. K. Patel, M. Gangar, K. Kumar, V. A. Nair, RSC Adv. 2015, 5, 3187-3195; (c) V. Kumar, K. Kumar, A. Pal, G. L. Khatik, V. A. Nair, Tetrahedron  2013,  69, 1747-1754; (d) K. Kumar, S. R. Mudshinge, S. Goyal, M. Gangar, V. A. Nair, Tetrahedron Lett. 2015, 56, 1266-1271; (e) M. Chouhan, K. R. Senwar, K. Kumar, R. Sharma, V. A. Nair, Synthesis 2014, 46, 195-202; (f) R. Sharma, K. Kumar, M. Chouhan, V. Grover, V. A.Nair,RSC Adv. 2013, 3, 14521-14527; (g) R. Kaur, K. Kumar, Chem. Heterocycl. Comp. 2018, 54, 700-702.

26. (a) S. Goyal, B. K. Patel, R. Sharma, M. Chouhan, K. Kumar, M. Gangar, V. A. Nair, Tetrahedron Lett. 2015, 56, 5409-5412; (b) K. Kumar, S. S. More, S. Goyal, M. Gangar, G. L. Khatik, R. K. Rawal, V. A. Nair, Tetrahedron Lett. 2016, 57,  2315-2319; (c) K. Kumar, J. Siddique, M. Gangar, S. Goyal, R. K. Rawal, V. A.Nair, Chem. Select 2016, 1, 2409-2412; (d) K. Kumar, D. Konar, S. Goyal, M. Gangar, M. Chouhan, R. K. Rawal, V. A. Nair, Chem. Select. 2016, 1, 3228-3231; (e) K. Kumar, D. Konar, S. Goyal, M. Gangar, M. Chouhan, R. K. Rawal, V. A. Nair, J. Org. Chem. 2016, 81, 9757-9764; (f) K. Kumar, S. S. More, G. L. Khatik, R. K. Rawal, V. A. Nair, J. Heterocycl. Chem. 2017, 54, 2696-2702; (g) R. Kaur, S. K. Manjal, R. K. Rawal, K. Kumar, Bioorg. Med. Chem. 2017, 25, 4533-4552; (h) S. K. Manjal, R. Kaur, R. Bhatia, K. Kumar, V. Singh, R. Shankar, R. Kaur, R. K. Rawal, Bioorg. Chem. 2017, 75, 406-423.

27. (a) M. Mittal, K. Kumar, D. Anghore, R. K. Rawal, Curr. Drug Discover. Tech. 2017, 14,  106-120; (b) R. Kaur, S. Choudhary, K. Kumar, M. K. Gupta, R. K. Rawal, Eur. J. Med. Chem. 2017, 132, 108-134; (c) B. Kumar, V. Singh, R. Shankar, K. Kumar, R. K. Rawal, Curr. Topics. Med. Chem. 2017, 17, 148-161; (d) P. Talwan, S. Choudhary, K. Kumar, R. K. Rawal, Curr. Bioact. Compd. 2017, 13, 109-120; (e) R. Kaur, V. Rani, V. Abbot, Y. Kapoor, D. Konar, K. Kumar, J. Pharm. Chem. Chem. Sci. 2017, 1, 17-32.