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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 3, pp 249–268 | Cite as

Metal-catalyzed synthesis of five-membered ring N-heterocycles. A recent update

  • George VarvounisEmail author
  • Ioannis E. Gerontitis
  • Vasileios Gkalpinos
Article

The review deals with the metal-catalyzed synthetic methods used for the construction of 5-membered nitrogen-containing aromatic and nonaromatic heterocycles with one to three nitrogen atoms, published in the years 2008–2017. The methodology is based on the metalcatalyzed activation of the alkyl C(sp3)–H, alkenyl C(sp2)–H, and terminal alkyne C(sp)–H bonds of appropriate precursors in order to perform intermolecular and intramolecular reactions. These bond forming reactions include C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp2)–C(sp) coupling, hydroamination at C(sp2)–H and C(sp)–H bonds, and oxidative amination of alkyl C(sp3)–H, alkenyl and arene C(sp2)–H, and terminal alkyne C(sp)–H bonds. Two further bond forming methods are intramolecular nitrenoid–arene C(sp2) coupling and cycloaddition reactions. Transition metals are systematically used in these synthetic methods, and only in a few cases Lewis acids are used as catalysts. In general, the metal-catalyzed cyclizations leading to five-membered heterocycles are very efficient and particularly useful in the synthesis of natural and unnatural biologically active products.

Keywords

five-membered N-heterocycles C–H bond activation C–H bond hydroamination C–H bond oxidative amination metalcatalyzed synthesis 

References

  1. 1.
    d'Ischia, M.; Napolitano, A.; Pezzella, A. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2008, Vol. 3, p. 353.Google Scholar
  2. 2.
    Marcantoni, E.; Petrini, M. Adv. Synth. Catal. 2016, 358, 3657.CrossRefGoogle Scholar
  3. 3.
    Majumdar, K. C.; Debnah, P.; De, N.; Roy, B. Curr. Org. Chem. 2011, 15, 1760.CrossRefGoogle Scholar
  4. 4.
    Zheng, Z.; Wang, Z.; Wang, Y.; Zhang, L. Chem. Soc. Rev. 2016, 45, 4448.CrossRefPubMedGoogle Scholar
  5. 5.
    Liu, T.; Fu, H. Synthesis 2012, 2805.Google Scholar
  6. 6.
    Wu, F. X.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1.CrossRefPubMedGoogle Scholar
  7. 7.
    Majumdar, K. C.; De, N.; Ghosh, T.; Roy, B. Tetrahedron 2014, 70, 4827.CrossRefGoogle Scholar
  8. 8.
    Nandakumar, A.; Midya, P. S.; Lange, V. G.; Balaraman, E. Angew. Chem., Int. Ed. 2015, 54, 11022.Google Scholar
  9. 9.
    Yuan, J.; Liu, C.; Lei, A. Chem. Comm. 2015, 1394.Google Scholar
  10. 10.
    Keiko, N. A.; Vchislo, N. V. Asian J. Org. Chem. 2016, 5, 439.CrossRefGoogle Scholar
  11. 11.
    Chen, W. W.; Xu, H. M. Org. Biomol. Chem. 2017, 15, 1029.CrossRefPubMedGoogle Scholar
  12. 12.
    Hennessy, E. T.; Betley, T. A. Science 2013, 340, 591.CrossRefPubMedGoogle Scholar
  13. 13.
    Perez, S. J.; Purino, A. M.; Cruz, A. D.; Lopez-Soria, M. J.; Carballo, M. R.; Ramirez, A. M.; Fernandez, I.; Martin, S. V.; Padron, I. J. Chem.–Eur. J. 2016, 22, 15529.CrossRefPubMedGoogle Scholar
  14. 14.
    Ji, K.-G.; Shu, X.-Z.; Zhao, S.-C.; Zhu, H.-T.; Niu, Y.-N.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2009, 11, 3206.CrossRefPubMedGoogle Scholar
  15. 15.
    Praveen, C.; Montaignac, B.; Vitale, M. R.; Ratovelomanana-Vidal, V.; Michelet, V. Chem. Cat. Chem. 2013, 5, 2395.Google Scholar
  16. 16.
    Lazzara, P. R.; Fitzpatrick, K. P.; Eichman, C. C. Chem.–Eur. J. 2016, 22, 16779.CrossRefPubMedGoogle Scholar
  17. 17.
    Han, J.; Xu, B.; Hammond, G. B. J. Am. Chem. Soc. 2010, 132, 916.CrossRefPubMedGoogle Scholar
  18. 18.
    Wang, B.; Liang, M.; Tang, J.; Deng, Y.; Zhao, J.; Sun, H.; Tung, C.-H.; Jia, J.; Xu, Z. Org. Lett. 2016, 18, 4614.CrossRefPubMedGoogle Scholar
  19. 19.
    Fuller, P. H.; Kim, J.; Chemler, S. R. J. Am. Chem. Soc. 2008, 130, 17638.CrossRefPubMedPubMedCentralGoogle Scholar
  20. 20.
    Paderes, M. C.; Keister, J. B.; Chemler, S. R. J. Org. Chem. 2013, 78, 506.CrossRefPubMedGoogle Scholar
  21. 21.
    Lin, M.; Li, F.; Jiao, L.; Yu, Z.-X. J. Am. Chem. Soc. 2011, 133, 1690.CrossRefPubMedGoogle Scholar
  22. 22.
    Zhang, W.; Dong, X.; Zhao, W. Org. Lett. 2011, 13, 5386.CrossRefPubMedGoogle Scholar
  23. 23.
    Trost, B. M.; Silverman, S. M. J. Am. Chem. Soc. 2010, 132, 8238.CrossRefPubMedGoogle Scholar
  24. 24.
    Gao, P.; Yan, X.-B.; Tao, T.; Yang, F.; He, T.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M. Chem.–Eur. J. 2013, 19, 14420.CrossRefPubMedGoogle Scholar
  25. 25.
    Caruano, J.; Muccioli, G. G.; Robiette, R. Org. Biomol. Chem. 2016, 14, 10134.CrossRefPubMedGoogle Scholar
  26. 26.
    Kaur, N. Synth. Commun. 2015, 45, 432.CrossRefGoogle Scholar
  27. 27.
    Coussanes, G.; Vila, X.; Diaba, F.; Bonjoch, J. Synthesis 2017, 1481.Google Scholar
  28. 28.
    He, G.; Zhang, S.-Y.; Nack, W. A.; Li, Q.; Chen, G. Angew. Chem., Int. Ed. 2013, 52, 11124.Google Scholar
  29. 29.
    Qi, J.; Sun, C.; Tian, Y.; Wang, X.; Li, G.; Xiao, Q.; Yin, D. Org. Lett. 2014, 16, 190.CrossRefPubMedGoogle Scholar
  30. 30.
    Obniska, J.; Rzepka, S.; Kamiński, K. Bioorg. Med. Chem. 2012, 20, 4872.CrossRefPubMedGoogle Scholar
  31. 31.
    Ha, Y. M.; Kim, J.; Park, Y.-J.; Park, D. Choi, Y.-J.; Kim, J.-M.; Chung, K.-W.; Han, Y.-K.; Park, J.-Y.; Lee, J.-Y.; Moon, H.-R.; Chung, H.-Y. Med. Chem. Commun. 2011, 2, 542.CrossRefGoogle Scholar
  32. 32.
    Shaikh, T. M.; Hong, F. E. J. Organomet. Chem. 2016, 801, 139.CrossRefGoogle Scholar
  33. 33.
    Hasegawa, N.; Charra, V.; Inoue, S.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 8070.CrossRefPubMedGoogle Scholar
  34. 34.
    Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.CrossRefGoogle Scholar
  35. 35.
    Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213.CrossRefGoogle Scholar
  36. 36.
    Anderson, K. W.; Milowsky, S. A. J. Med. Chem. 1987, 30, 2144.CrossRefPubMedGoogle Scholar
  37. 37.
    Brown, C. H.; Vara Prasad, J. V. N.; Gupta, A. K. J. Org. Chem. 1986, 51, 4296.CrossRefGoogle Scholar
  38. 38.
    Candeias, N. R.; Branco, L. C.; Gois, P. M. P.; Alfonso, C. A. M.; Trindade, A. F. Chem. Rev. 2009, 109, 2703.CrossRefPubMedGoogle Scholar
  39. 39.
    Amombo, G. M. O.; Flogel, O.; Kalai, S. K. D.; Schoder, S.; Warzok, U.; Ressig, H.-U. Eur. J. Org. Chem. 2017, 1965.Google Scholar
  40. 40.
    Chung, M.-C.; Chan, Y.-H.; Chang, W.-J.; Hou, D.-R. Org. Biomol. Chem. 2017, 15, 3783.CrossRefPubMedGoogle Scholar
  41. 41.
    Jiang, B.; Meng, F.-F.; Liang, Q.-J.; Xu, Y.-H.; Loh, T.-P. Org. Lett. 2017, 19, 914.CrossRefPubMedGoogle Scholar
  42. 42.
    Faulkner, A.; Bower, J. F. Angew. Chem., Int. Ed. 2012, 51, 1675.CrossRefGoogle Scholar
  43. 43.
    Thansandote, P.; Lautens, M. Chem.–Eur. J. 2009, 15, 5874.CrossRefPubMedGoogle Scholar
  44. 44.
    Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Aldrichimica Acta 2010, 43, 37.PubMedPubMedCentralGoogle Scholar
  45. 45.
    Jiang, B.; Rajale, T.; Wever, W.; Tu, S.-J.; Li, G. Chem.–Asian J. 2010, 5, 2318.Google Scholar
  46. 46.
    Schranck, J.; Tlili, A.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 7642.CrossRefGoogle Scholar
  47. 47.
    Guo, X.-X.; Gu, D.-W.; Wu, Z.; Zhang, W. Chem. Rev. 2015, 115, 1622.CrossRefPubMedGoogle Scholar
  48. 48.
    Yoshikai, N.; Wei, Y. Asian J. Org. Chem. 2013, 2, 466.Google Scholar
  49. 49.
    Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev. 2015, 44, 1155.CrossRefPubMedGoogle Scholar
  50. 50.
    Dorel, R.; Echavarren, M. A. Chem. Rev. 2015, 115, 9028.CrossRefPubMedPubMedCentralGoogle Scholar
  51. 51.
    Cravotto, G.; Tagliapietra, S.; Caporaso, M.; Garella, D.; Borretto, E.; Di Stilo, A. Chem. Heterocycl. Compd. 2013, 49, 811. [Khim. Geterotsikl. Soedin. 2013, 869.]Google Scholar
  52. 52.
    Kaur, N. Synth. Comm. 2015, 45, 539.CrossRefGoogle Scholar
  53. 53.
    Pan, D.; Wei, Y.; Shi, M. Org. Lett. 2016, 18, 3930.CrossRefPubMedGoogle Scholar
  54. 54.
    Chen, W.; Wang, J. Organometallics 2013, 32, 1958.CrossRefGoogle Scholar
  55. 55.
    Chiba, S.; Wang, Y.-F.; Lapointe, G.; Narasaka, K. Org. Lett. 2008, 10, 313.CrossRefPubMedGoogle Scholar
  56. 56.
    Wang, H.; Grohmann, C.; Nimphius, C.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 19592.CrossRefPubMedGoogle Scholar
  57. 57.
    Ngwerume, S.; Lewis, W.; Camp, J. E. J. Org. Chem. 2013, 78, 920.CrossRefPubMedGoogle Scholar
  58. 58.
    Chan, C.-M.; Zhou, Z.; Yu, W.-Y. Adv. Synth. Catal. 2016, 358, 4067.CrossRefGoogle Scholar
  59. 59.
    Gao, M.; He, C.; Hongyi, C.; Bai, R.; Cheng, B.; Lei, A. Angew. Chem., Int. Ed. 2013, 52, 6958.CrossRefGoogle Scholar
  60. 60.
    Doan, P.; Karjalainen, A.; Chandraseelan, J. G.; Sandberg, O.; Yli-Harja, O.; Rosholm, T.; Franzen, R.; Candeias, N. R.; Kandhavelu, M. Eur. J. Med. Chem. 2016, 120, 296.CrossRefPubMedGoogle Scholar
  61. 61.
    Minati, A.; Buchwald, S. L. Org. Lett. 2008, 10, 2721.CrossRefGoogle Scholar
  62. 62.
    Sodeoka, M.; Egami, H. Pure Appl. Chem. 2014, 86, 1247.CrossRefGoogle Scholar
  63. 63.
    Stokes, B. J.; Driver, T. G. Eur. J. Org. Chem. 2011, 4071.Google Scholar
  64. 64.
    Baudoin, O. Acc. Chem. Res. 2017, 50, 1114.CrossRefPubMedGoogle Scholar
  65. 65.
    Phillips, D.; France, D. J. Asian J. Org. Chem. 2017, 6, 27.CrossRefGoogle Scholar
  66. 66.
    Lemen, G. S.; Wolfe, J. P. Org. Lett. 2011, 13, 3218.CrossRefPubMedPubMedCentralGoogle Scholar
  67. 67.
    Guyonnet, M.; Baudoin, O. Org. Lett. 2012, 14, 398.CrossRefPubMedGoogle Scholar
  68. 68.
    Rousseaux, S.; Davi, M.; Julien Sofack-Kreutzer, J.; Pierre, C.; Kefalidis, C. E.; Clot, E.; Fagnou, K.; Baudoin, O. J. Am. Chem. Soc. 2010, 132, 10706.CrossRefPubMedGoogle Scholar
  69. 69.
    Liao, J.; Fan, L.; Guo, W.; Zhang, Z.; Li, J.; Zhu, C.; Ren, Y.; Wu, W.; Jiang, H. Org. Lett. 2017, 19, 1008.CrossRefPubMedGoogle Scholar
  70. 70.
    Sequeira, F. C.; Bovino, M. T.; Chipre, A. J.; Chemler, S. R. Synthesis 2012, 1481.Google Scholar
  71. 71.
    Santi, M.; Muller, T. S. R.; Folgueiras-Amador, A. A.; Uttry, A.; Hellier, P.; Wirth, T. Eur. J. Org. Chem. 2017, 1889.Google Scholar
  72. 72.
    Ascic, E.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 4666.CrossRefPubMedPubMedCentralGoogle Scholar
  73. 73.
    Dateer, R. B.; Chang, S. J. Am. Chem. Soc. 2015, 137, 4908.CrossRefPubMedGoogle Scholar
  74. 74.
    Dalpozzo, R. Adv. Synth. Catal. 2017, 359, 1772.CrossRefGoogle Scholar
  75. 75.
    Millemaggi, A.; Taylor, R. J. K. Eur. J. Org. Chem. 2010, 4527.Google Scholar
  76. 76.
    Youn, S. W. Eur. J. Org. Chem. 2009, 2597.Google Scholar
  77. 77.
    Xu, P.; Xie, J.; Xue, Q.; Pan, C.; Cheng, Y.; Zhu, C. Chem.–Eur. J. 2013, 19, 14039.CrossRefPubMedGoogle Scholar
  78. 78.
    Li, Z.; Cui, X.; Niu, L.; Ren, Y.; Bian, M.; Yang, X.; Yang, B.; Yan, Q.; Zhao, J. Adv. Synth. Catal. 2017, 359, 246.CrossRefGoogle Scholar
  79. 79.
    Li, Y.; Shi, Y.; Huang, Z.; Wu, X.; Xu, P.; Wang, J.; Zhang, Y. Org. Lett. 2011, 13, 1210.CrossRefPubMedGoogle Scholar
  80. 80.
    Li, Y.-J; Yan, N.; Liu, C.-H.; Yu, Y.; Zhao, Y.-L. Org. Lett. 2017, 19, 1160.CrossRefPubMedGoogle Scholar
  81. 81.
    Di Mola, A.; Tiffner, M.; Scorzelli, F.; Palombi, L.; Filosa, R.; De Caprariis, P.; Waser, M.; Massa, M. Beilstein J. Org. Chem. 2015, 11, 2591.Google Scholar
  82. 82.
    Zhu, C.; Falck, J. R. Chem. Commun. 2012, 48, 1674.CrossRefGoogle Scholar
  83. 83.
    Pathare, R. S.; Sharma, S.; Elagandhula, S.; Saini, V.; Sawant, D. M.; Yadav, M.; Sharon, A.; Khan, S.; Pardasani, R. T. Eur. J. Org. Chem. 2016, 5579.Google Scholar
  84. 84.
    Tobisu, M.; Chatani, N. Chem. Lett. 2011, 40, 330.CrossRefGoogle Scholar
  85. 85.
    Jana, N.; Driver, T. G. Org. Biomol. Chem. 2015, 13, 9720.CrossRefPubMedGoogle Scholar
  86. 86.
    Lin, H.; Kazmaier, U. Eur. J. Org. Chem. 2009, 1221.Google Scholar
  87. 87.
    Pedroni, J.; Cramer, N. Org. Lett. 2016, 18, 1932.CrossRefPubMedGoogle Scholar
  88. 88.
    Baxter, C. A.; Cleator, E.; Alam, M.; Davies, A. J.; Goodyear, A.; O'Hagan, M. Org. Lett. 2010, 12, 668.CrossRefPubMedGoogle Scholar
  89. 89.
    Patel, P.; Borah, G. Eur. J. Org. Chem. 2017, 2272.Google Scholar
  90. 90.
    Schmidt, A. W.; Reddy, K. R.; Knölker, H.-J. Chem. Rev. 2012, 112, 3193.CrossRefPubMedGoogle Scholar
  91. 91.
    Chiusoli, G. P.; Catellani, M.; Costa, M.; Motti, E.; Della Ca’, N.; Maestri, G. Coord. Chem. Rev. 2010, 254, 456.CrossRefGoogle Scholar
  92. 92.
    Kaur, N. Catal. Rev.: Sci. Eng. 2015, 57, 1.CrossRefGoogle Scholar
  93. 93.
    Cadogan, J. I. G. Synthesis 1969, 11.Google Scholar
  94. 94.
    Gao, H.; Xu, Q. L.; Yousufuddin, M.; Ess, D. H.; Kürti, L. Angew. Chem., Int. Ed. 2014, 53, 2701.Google Scholar
  95. 95.
    Monguchi, Y.; Okami, H.; Ichikawa, T.; Nozaki, K.; Maejima, T.; Oumi, Y.; Sawama, Y.; Sajiki, H. Adv. Synth. atal. 2016, 358, 3145.CrossRefGoogle Scholar
  96. 96.
    Bjørsvik, H.-R.; Elumalai, V. Eur. J. Org. Chem. 2016, 5474.Google Scholar
  97. 97.
    Yang, L.; Li, H.; Zhang, H.; Lu, H. Eur. J. Org. Chem. 2016, 5611.Google Scholar
  98. 98.
    Liu, Z.; Larock, R. C. Tetrahedron 2007, 63, 347.CrossRefPubMedPubMedCentralGoogle Scholar
  99. 99.
    Ackermann, L.; Althammer, A. Angew. Chem., Int. Ed. 2007, 46, 1627.CrossRefGoogle Scholar
  100. 100.
    Uwa, K.; Tseng, Y.-Y.; Kamikawa, K. Eur. J. Org. Chem. 2017, 892.Google Scholar
  101. 101.
    De Luca, L. Curr. Med. Chem. 2006, 13, 1.Google Scholar
  102. 102.
    Zhang, L.; Peng, X.-M.; Damu, G. L. V.; Geng, R.-X.; Zhou, C.-H. Med. Res. Rev. 2014, 34, 340.CrossRefPubMedGoogle Scholar
  103. 103.
    Chiba, S. Tetrahedron Lett. 2016, 57, 3678.CrossRefGoogle Scholar
  104. 104.
    Ma, H.; Zhang, X.; Chen, L.; Yu, W. J. Org. Chem. 2017, 82, 11841.CrossRefPubMedGoogle Scholar
  105. 105.
    Zeng, Z.; Jin, H.; Xie, J.; Tian, B.; Rudolf, M.; Rominger, F.; Hashmi, A. S. K. Org. Lett. 2017, 19, 1020.CrossRefPubMedGoogle Scholar
  106. 106.
    Keri, R. S.; Hiremathad, A.; Budagumpi, S.; Nagaraja, B. M. Chem. Biol. Drug Des. 2015, 86, 19.CrossRefPubMedGoogle Scholar
  107. 107.
    Barot, K. P.; Nikolova, S.; Ivanov, I.; Ghate, M. D. Mini-Rev. Med. Chem. 2013, 13, 1421.CrossRefPubMedGoogle Scholar
  108. 108.
    Bansal, Y.; Silakari, O. Bioorg. Med. Chem. 2012, 20, 6208.CrossRefPubMedGoogle Scholar
  109. 109.
    Majumdar, K. C.; Roy, B.; Dbnath, P.; Taher, A. Cur. Org. Chem. 2010, 14, 846.CrossRefGoogle Scholar
  110. 110.
    Peng, J.; Ye, M.; Zong, C.; Hu, F.; Feng, L.; Wang, X.; Wang, Y.; Chen, C. J. Org. Chem. 2011, 76, 716.CrossRefPubMedGoogle Scholar
  111. 111.
    Liu, J.; Wang, C.; Ma, X.; Shi, X.; Wang, X.; Li, H.; Xu, Q. Catal. Lett. 2016, 146, 2139.CrossRefGoogle Scholar
  112. 112.
    Mahesh, D.; Satheesh, V.; Kumar, S. V.; Punniyamurthy, T. Org. Lett. 2017, 19, 6554.CrossRefPubMedGoogle Scholar
  113. 113.
    Faraz, K. M.; Garima, V.; Wasim, A.; Akranth, M.; Mumtaz, A. M.; Mymoona, A.; Asif, H.; Misbahul, H. S.; Mohammad, S.; Rashiduddin, H. S. Int. J. Drug Dev. & Res. 2017, 9(2), 22.Google Scholar
  114. 114.
    Lauria, A.; Delisi, R.; Mingoia, F.; Terenzi, A.;Martorana, A.; Barone, G.; Almerico, A. M. Eur. J. Org. Chem. 2014, 3289.Google Scholar
  115. 115.
    Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.CrossRefPubMedGoogle Scholar
  116. 116.
    Chen, Z.; Yan, Q.; Liu, Z.; Xu, Y.; Zhang, Y. Angew. Chem., Int. Ed. 2013, 52, 13324.CrossRefGoogle Scholar
  117. 117.
    Daştan, A.; Kulkarni A.; Török, B. Green Chem. 2012, 14, 17.CrossRefGoogle Scholar
  118. 118.
    Kaur, N. Synth. Comm. 2015, 45, 1711.CrossRefGoogle Scholar
  119. 119.
    Chen, Z.; Liu, Z.; Cao, G.; Li, H.; Ren, H. Adv. Synth. Catal. 2017, 359, 202.CrossRefGoogle Scholar
  120. 120.
    Phanindrudu, M.; Tiwari, D. K.; Aravilli, V. K.; Bhardwaj, K. C.; Sabapathi, G.; Likhar, P. R.; Tiwari, D. K. Eur. J. Org. Chem. 2016, 4629.Google Scholar
  121. 121.
    Gabba, A.; Robakiewicz, S.; Taciak, B.; Ulewicz, K.; Broggini, G.; Rastelli, G.; Krol, M.; Murphy, P. V.; Passarella, D. Eur. J. Org. Chem. 2017, 60.Google Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • George Varvounis
    • 1
    Email author
  • Ioannis E. Gerontitis
    • 1
  • Vasileios Gkalpinos
    • 1
  1. 1.Section of Organic Chemistry and Biochemistry, Department of ChemistryUniversity of IoanninaIoanninaGreece

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