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Stereo-selective green protocol for the synthesis of highly substituted 1-phenyl-tetrahydro indeno [1, 2-b]pyrroles

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Abstract

Simple, one step, stereo selective and green domino strategies for the synthesis of substituted indeno [1, 2, b]pyrrole analogues in good yield without column purification have been established successfully. This method describing the advantages such as high atom economy, eco-friendliness, easy isolation of products, good yields, energy efficiency and no column purification.

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References

  1. B. Jiang, Q.Y. Li, S. Jiang, G. Li, Org. Lett. 14, 5210 (2012)

    Article  CAS  Google Scholar 

  2. M.Y. San, X.Y. Meng, F.J. Zhao, Y.J. Dang, F. Joang, K. Liu, C.S. Wang, B. Jiang, S.J. Tu, Eur. J. Org. Chem. 17, 3690 (2014)

    Article  Google Scholar 

  3. Z.W. Chen, J.B. Hou, Z.R. Dai, X.F. Yang, Chin. Chem. Lett. 27, 1622 (2016)

    Article  CAS  Google Scholar 

  4. A. Fürstner, Angew. Chem. Int. Ed. 42, 3582 (2003)

    Article  Google Scholar 

  5. F. Bellina, R. Rossi, Tetrahedron 62, 7213 (2006)

    Article  CAS  Google Scholar 

  6. P.A. Jacobi, L.D. Coutts, J. Guo, S.I. Hauck, S.H. Leung, J. Org. Chem. 65, 205 (2000)

    Article  CAS  Google Scholar 

  7. V. Estevez, M. Villacampa, J.C. Menendez, Chem. Soc. Rev. 43, 4633 (2014)

    Article  CAS  Google Scholar 

  8. J.L. Sessler, D. An, W.-S. Cho, V.M. Lynch, Angew. Chem. Int. Ed. 42, 2278 (2003)

    Article  CAS  Google Scholar 

  9. J.L. Sessler, D. An, W.-S. Cho, V.M. Lynch, J. Am. Chem. Soc. 125, 13646 (2003)

    Article  CAS  Google Scholar 

  10. T. Fukuda, F. Ishibashi, M. Iwao, Heterocycles 83, 491 (2011)

    Article  CAS  Google Scholar 

  11. D.P. O’Malley, K. Li, M. Maue, A.L. Zografos, P.S. Baran, J. Am. Chem. Soc. 129, 4762 (2007)

    Article  Google Scholar 

  12. J.A. Nieman, M.D. Ennis, Org. Lett. 2, 1395 (2000)

    Article  CAS  Google Scholar 

  13. B.B. Snider, Y. Ahn, B.M. Foxman, Tetrahedron Lett. 40, 3337 (1999)

    Article  Google Scholar 

  14. C.J. Lovely, H. Mahmud, Tetrahedron Lett. 40, 2079 (1999)

    Article  CAS  Google Scholar 

  15. K.M. Witherup, R.M. Ransom, A.C. Graham, A.M. Bernard, M.J. Salvatore, W.C. Lumma, P.S. Anderson, S.M. Pitzenberger, S.L. Varga, J. Am. Chem. Soc. 117, 6682 (1995)

    Article  CAS  Google Scholar 

  16. A. Furstner, Angew. Chem. Int. Ed. 42, 3528 (2003)

    Google Scholar 

  17. A. Furstner, H. Szillat, B. Gabor, R. Mynott, J. Am. Chem. Soc. 120, 8305 (1998)

    Article  Google Scholar 

  18. B.H. Lipshutz, Chem. Rev. 86, 795 (1986)

    Article  CAS  Google Scholar 

  19. G. Balme, Angew. Chem. Int. Ed. 43, 6238 (2004)

    Article  CAS  Google Scholar 

  20. X. Fu, J. Chen, G. Li, Y. Liu, Angew. Chem. Int. Ed. 48, 5500 (2009)

    Article  CAS  Google Scholar 

  21. A.U. De, B.P. Saha, J. Pharm. Sci. 62, 1363 (1973)

    Article  CAS  Google Scholar 

  22. F. Rostami-Charati, Chinese. Chem. Lett. 25, 169 (2014)

    CAS  Google Scholar 

  23. M.R. Mohammadizadeh, M. Bahramzadeh, S.Z. Taghavi, Tetrahedron Lett. 51, 5807 (2010)

    Article  CAS  Google Scholar 

  24. F. Yang, H. Wang, L. Jiang, H. Yue, H. Zhang, Z. Wang, L. Wang, RSC Adv. 5, 5213 (2015)

    Article  CAS  Google Scholar 

  25. A. UlaczykLesanko, D.G. Hall, Curr. Opin. Chem. Biol. 9, 266 (2005)

    Article  CAS  Google Scholar 

  26. B.B. Toure, D.G. Hall, Chem. Rev. 109, 4439 (2009)

    Article  CAS  Google Scholar 

  27. S. Perreault, T. Rovis, Chem. Soc. Rev. 38, 3149 (2009)

    Article  CAS  Google Scholar 

  28. M. Baumann, I.R. Baxendale, S.V. Ley, N. Nikbin, Beilstein J. Org. Chem. 7, 442 (2011)

    Article  CAS  Google Scholar 

  29. V. Estévez, M. Villacampa, J.C. Menéndez, Chem. Commun. 49, 591 (2013)

    Article  Google Scholar 

  30. A. Nicholas, M.A. Magnus, U.E. Staszak, U.J.P. Wepsiec, Org. Process Res. Dev. 10, 899 (2006)

    Article  Google Scholar 

  31. M. Sulur, P. Sharma, R. Ramakrishnan, R. Naidu, E. Merifield, D.M. Gill, A.M. Clarke, C. Thomson, M. Butters, S. Bachu, C.H. Benison, N. Dokka, E.R. Fong, D.R.J. Hose, G.P. Howell, S.E. Mobberley, S.C. Morton, A.K. Mullen, J. Rapai, B. Tejas, Org. Process Res. Dev. 16, 1746 (2012)

    Article  CAS  Google Scholar 

  32. J.S. Moore, K.F. Jensen, Org. Process Res. Dev. 16, 1409 (2012)

    Article  CAS  Google Scholar 

  33. V. Estevez, M. Villacampa, C. Menendez, J. Chem. Commun. 49, 591 (2012)

    Article  Google Scholar 

  34. A. Herath, N.D.P. Cosford, Org. Lett. 12, 5182 (2010)

    Article  CAS  Google Scholar 

  35. B. Li, N. Wang, Y. Liang, S. Xu, B. Wang, Org. Lett. 15, 136 (2013)

    Article  CAS  Google Scholar 

  36. A. Hantzsch, Ber. Dtsch. Chem. Ges. 23, 1474 (1890)

    Article  Google Scholar 

  37. V. Jeyachandran, M. Muthu, R.R. Kumar, Synth. Commun. 45, 1137 (2015)

    Article  CAS  Google Scholar 

  38. S. Ngwerume, J.E. Camp, J. Org. Chem. 75, 6271 (2010)

    Article  CAS  Google Scholar 

  39. M.R.R.S.L. Buchwald, Org. Lett. 9, 973 (2007)

    Article  Google Scholar 

  40. Y. Jiang, W.C. Chan, C.-M. Park, J. Am. Chem. Soc. 134, 4104 (2012)

    Article  CAS  Google Scholar 

  41. S. Ngwerume, W. Lewis, J.E. Camp, J. Org. Chem. 78, 920 (2013)

    Article  CAS  Google Scholar 

  42. G.A. Pinna, M.M. Curzu, M. Sechi, G. Chelucci, Maciocco. E. Farmaco 54, 542 (1999)

    Article  CAS  Google Scholar 

  43. S. Hanessian, G. Papeo, M. Angiolini, K. Fettis, M. Berettaand, A. Munro, J. Org. Chem. 68, 7204 (2003)

    Article  CAS  Google Scholar 

  44. M. Pour, M. Spulak, V. Buchta, J. Med. Chem. 44, 2701 (2001)

    Article  CAS  Google Scholar 

  45. E. Lattmann, N. Sattayasai, C.S. Schwalbe, Curr. Drug Discov. Technol. 3, 125 (2006)

    Article  CAS  Google Scholar 

  46. G. Burton, T.W. Ku, T.J. Carr, T. Kiesow, R.T. Sarisky, J. Lin Goerke, G.A. Hofmann, M.J. Slater, D. Haigh, D. Dhanak, V.K. Johnson, N.R. Parry, P. Thommes, Bio org. Med. Chem. Lett. 17, 1930 (2007)

    Article  CAS  Google Scholar 

  47. E. Spink, D. Ding, Z. Peng, M.A. Boudreau, E. Leemans, E. Lastochkin, W. Song, K. Lichtenwalter, P.I. O’Daniel, S.A. Testero, H. Pi, V.A. Schroeder, W.R. Wolter, N.T. Antunes, M.A. Suckow, S. Vakulenko, M. Chang, S. Mobashery, J. Med. Chem. 58, 1380 (2015)

    Article  CAS  Google Scholar 

  48. N.N. Pham, T.T. Dang, N.T. Ngo, A. Villinger, P. Ehlers, P. Langer, Org. Biomol. Chem. 13, 6047 (2015)

    Article  CAS  Google Scholar 

  49. J. Lehuede, B. Fauconneau, L. Barrier, M. Ourakow, A. Piriou, J.M. Vierfond, Eur. J. Med. Chem. 34, 991 (1999)

    Article  CAS  Google Scholar 

  50. R.W. Burli, D. McMinn, J.A. Kaizerman, W. Hu, Y. Ge, Q. Pack, V. Jiang, M. Gross, M. Garcia, R. Tanaka, H.E. Moser, Bio. Org. Med. Chem. Lett. 14, 1253 (2004)

    Article  CAS  Google Scholar 

  51. E. Toja, D. Selva, P. Schiatti, J. Med. Chem. 27, 610 (1984)

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

  53. X. Han, W. Ouyang, B. Liu, W. Wang, P. Tien, S. Wu, H.-B. Zhou, Org. Biomol. Chem. 11, 8463 (2013)

    Article  CAS  Google Scholar 

  54. R.L. Ragno, G.R. Marshall, R.D. Santo, R. Costi, S. Massa, R. Rompei, M. Artico, Bio. Org. Med. Chem. 8, 1423 (2000)

    Article  CAS  Google Scholar 

  55. J. Yu, F. Shi, L.Z. Gong, Acc. Chem. Res. 44, 1156 (2011)

    Article  CAS  Google Scholar 

  56. Y.M. Wang, H.H. Zhang, C. Li, T. Fan, F. Shi, Chem. Commun. 52, 1804 (2016)

    Article  CAS  Google Scholar 

  57. W. Dai, X.L. Jiang, J. Tao, Feng Shi. J. Org. Chem. 81, 185 (2016)

    Article  CAS  Google Scholar 

  58. W. Dai, X. Li Jiang, Q. Wu, F. Shi, S.J. Tu, J. Org. Chem. 80, 5737 (2015)

    Article  CAS  Google Scholar 

  59. Q. Zhu, Y.C. Zhang, M.M. Xu, X.X. Sun, X. Yang, F. Shi, J. Org. Chem. 81, 7898 (2016)

    Article  CAS  Google Scholar 

  60. A.U. De, B.P. Saha, J. Pharm. Sci. 62, 1363 (1973)

    Article  CAS  Google Scholar 

  61. S. Hanessian, G. Papeo, M. Angiolini, K. Fettis, M. Beretta, A. Munro, J. Org. Chem. 68, 7204 (2003)

    Article  CAS  Google Scholar 

  62. G.J. Alexander, L.M. Kopeloff, N. Chatterjie, Exp. Neurol. 89, 1 (1985)

    Article  CAS  Google Scholar 

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Acknowledgements

Authors are thankful to DST New Delhi for the high resolution NMR spectrometer under the IRHPA program.

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Correspondence to Vediappen Padmini.

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Kumar, M., Padmini, V. & Bhuvanesh, N. Stereo-selective green protocol for the synthesis of highly substituted 1-phenyl-tetrahydro indeno [1, 2-b]pyrroles. Res Chem Intermed 43, 4517–4530 (2017). https://doi.org/10.1007/s11164-017-2893-8

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