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A facile synthesis of diformylated pyrroles by dehydroxylation of N-aryl-5-hydroxy-γ-lactam derivatives under Vilsmeier reaction conditions

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A simple and efficient methodology for the conversion of substituted trans-1,4-diaryl-5-hydroxypyrrolidin-2-ones to diformylated N-arylpyrroles by treatment with Vilsmeier–Haack reagent has been developed.

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References

  1. (a) Curran, D.; Grimshaw, J.; Perera, S. D. Chem. Soc. Rev. 1991, 20, 391 and references therein. (b) Dong, C.; Deng, G.; Wang J. J. Org. Chem. 2006, 71, 5560.

  2. Bellur, E.; Freifeld, I.; Langer, P. Tetrahedron Lett. 2005, 47, 2151.

    Article  Google Scholar 

  3. (a) Reisser, M.; Maas, G. J. Org. Chem. 2004, 69, 4913. (b) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435. (c) Jendralla, H.; Baader, E.; Bartmann, W.; Beck, G.; Bergmann, A.; Granzer, E.; Von Kerekjarto, B.; Kesseler, K.; Krause, R.; Schubert, W.; Wess, G. J. Med. Chem. 1990, 33, 61. (d) Lee, C.-F.; Yang, L.-M.; Hwu, T.-Y.; Feng, A.-S.; Tseng, J.-C.; Luh, T.-Y. J. Am. Chem. Soc. 2000, 122, 4992. (e) Muchowski, J. M. Adv. Med. Chem. 1992, 1, 109. (f) Cozzi, P.; Mongelli, N. Curr. Pharm. Des. 1998, 4, 181. (g) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.

  4. Knorr, L. Ber. Dtsch. Chem. Ges. 1884, 17, 1635.

    Article  Google Scholar 

  5. (a) Banwell, M. G.; Goodwin, T. E.; Ng, S; Smith, J. A.; Wong, D. J. Eur. J. Org. Chem. 2006, 3043. (b) Shiraishi, H.; Nishitani, T.; Nishihara, T.; Sakaguchi, S.; Ishii, Y. Tetrahedron 1999, 55, 13957. (c) Zelikin, A.; Shastri, V. R.; Langer, R. J. Org. Chem. 1999, 64, 3379. (d) Liu, J.-H.; Chan, H.-W.; Wong, H. N. C. J. Org. Chem. 2000, 65, 3274. (e) Airaksinen, A. J.; Ahlgren, M.; Vepsalainen, J. J. Org. Chem. 2002, 67, 5019. (f) Smith, N. D.; Huang, D.; Cosford, N. D. P. Org. Lett. 2002, 4, 3537. (g) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855. (h) Verniest, G.; De Kimpe, N. Synlett 2003, 2013. (i) Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238. (j) Dhawan, R.; Arndtsen, B. A. J. Am. Chem. Soc. 2004, 126, 468. (j) De Kimpe, N.; Tehrani, K. A.; Stevens, C.; De Cooman, P. Tetrahedron 1997, 53, 3693. (k) Tehrani, K. A.; Borremans, D.; De Kimpe, N. Tetrahedron 1999, 55, 4133. (l) Verniest, G.; Claessens, S.; De Kimpe, N. Tetrahedron 2005, 61, 4631. (m) Verniest, G.; Claessens, S.; Bombeke, F.; Van Thienen, T.; De Kimpe, N. Tetrahedron 2005, 61, 2879. (n) Keppens, M.; De Kimpe, N.; Fonck, G. Synth. Commun. 1996, 26, 3097. (o) Surya Prakash Rao, H.; Jothilingam, S. Tetrahedron Lett. 2001, 42, 6595. (p) Minetto, G.; Raveglia, L. F.; Taddei, M. Org. Lett. 2004, 6, 389

  6. Barman, G.; Ray, J. K. Tetrahedron Lett. 2010, 51, 297.

    Article  CAS  Google Scholar 

  7. (a) Vilsmeier, A.; Haack, A. Ber. Dtsch. Chem. Ges. 1927, 60, 119. (b) Meth-Cohn, O.; Narine, B. Tetrahedron Lett. 1978, 19, 2045. (c) Khan, A. K.; Shoeb, A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985, 24, 62.

  8. (a) Jones, G.; Stanforth, S. P. Org. React. 1997, 49, 1. (b) Sreenivasulu, M.; Rao, K. G. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1989, 28, 584. (c) Mahata, P. K.; Venkatesh, C.; Syam Kumar, U. K.; Ila, H.; Junjappa, H. J. Org. Chem. 2003, 68, 3966. (d) Chupp, J. P.; Metz, S. J. Heterocycl. Chem. 1979, 16, 65. (e) Katrtizky, A. R.; Arend, M. J. Org. Chem. 1998, 63, 9989.

  9. (a) Haldar, P.; Barman, G.; Ray, J. K. Tetrahedron 2007, 63, 3049. (b) Barman, G.; Roy, M.; Ray, J. K. Tetrahedron Lett. 2008, 49, 1405. (c) Barman, G.; Ray, J. K. Synlett 2009, 20, 3333. (d) Barman, G.; Ray, J. K. J. Heterocycl. Chem. 2011, 48, 218. (e) Barman, G.; Haldar, P.; Dutta, N.; Ray, J. K. J. Heterocycl. Chem. 2011, 48, 463.

  10. Haldar, P.; Ray, J. K. Tetrahedron Lett. 2008, 49, 3659

    Article  CAS  Google Scholar 

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Correspondence to Gopa Barman.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 869–871

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Barman, G. A facile synthesis of diformylated pyrroles by dehydroxylation of N-aryl-5-hydroxy-γ-lactam derivatives under Vilsmeier reaction conditions. Chem Heterocycl Comp 51, 869–871 (2015). https://doi.org/10.1007/s10593-015-1789-z

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  • DOI: https://doi.org/10.1007/s10593-015-1789-z

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