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The use of N-halosuccinimides for cyclization with the formation of five-membered heterocyclic compounds

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The review summarizes the literature data for the period 2000–2017 on the most successful use of N-halosuccinimides in the preparative synthesis of five-membered heterocyclic compounds. The review is structured in accordance with the classification of the synthesized heterocycles with one (furans, thiophenes, selenophenes, pyrroles, and their analogs), two (oxazoles, isoxazoles, thiazoles, isothiazoles, pyrazoles, imidazoles), three (oxadiazoles, triazoles), or four heteroatoms (tetrazoles). The bibliography of the review includes 117 references to literary sources.

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References

  1. 1.

    (a) Koval', I. V. Russ. J. Org. Chem.2002, 38, 301. [Zh. Org. Khim.2002, 38, 327.] (b) Sniady, A. Synlett2006, 960. (c) Gołębiewski, W. M.; Gucma, M. Synthesis2007, 3599(d) Veisi, H.; Ghorbani-Vaghei, R.; Zolfigol, M. A. Org. Prep. Proc. Int.2011, 43, 489. (e) Saikia, I.; Borah, A. J.; Phukan, P. Chem. Rev.2016, 116, 6837.

  2. 2.

    (a) Veisi, H.; Ghorbani-Vaghei, R. Tetrahedron2010, 66, 7445. (b) de Andrade, V. S. C.; de Mattos, M. C. S. Curr. Green Chem.2018, 5, 68. (c) de Andrade, V. S. C.; de Mattos, M. C. S. Synthesis2019, 1841.

  3. 3.

    Ghasemnejad-Bosra, H.; Faraje, M.; Habibzadeh, S.; Ramzanian-Lehmali, F. J. Serb. Chem. Soc.2010, 75, 299.

  4. 4.

    Huang, W. B.; Liu, C. H.; Gu, Y. L. Adv. Synth. Catal.2017, 359, 1811.

  5. 5.

    (a) Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett.2005, 7, 1769. (b) Sniady, A.; Morreale, M. S.; Dembinski, R. Org. Synth.2007, 84, 199; 2009, Coll. Vol. 11, 794.

  6. 6.

    (a) Li, Y.; Wheeler, K. A.; Dembinski, R. Eur. J. Org. Chem.2011, 2767. (b) Li, Y.; Wheeler, K. A.; Dembinski, R. Org. Biomol. Chem.2012, 10, 2395.

  7. 7.

    Zhou, H.; Yao, J.; Liu, G. Tetrahedron Lett.2008, 49, 226.

  8. 8.

    Sasikala, K. A.; Kalesh, K. A.; Anabha, E. R.; Pillai, P. M.; Asokan, C. V.; Devaky, K. S. Tetrahedron Lett.2011, 52, 1667.

  9. 9.

    Hyland, C. J. T.; Hegedus, L. S. J. Org. Chem.2006, 71, 8658.

  10. 10.

    Zhao, Y.; Jiang, X.; Yeung, Y.-Y. Angew. Chem., Int. Ed.2013, 52, 8597.

  11. 11.

    Wei, Y.; Lin, S.; Zhang, J.; Niu, Z.; Fu, Q.; Liang, F. Chem. Commun.2011, 47, 12394.

  12. 12.

    Mothe, S. R.; Kothandaraman, P.; Rao, W.; Chan, P. W. H. J. Org. Chem.2011, 76, 2521.

  13. 13.

    Lee, A. S.-Y.; Tsao, K.-W.; Chang, Y.-T.; Chu, S.-F. Tetrahedron Lett. 2007, 48, 6790.

  14. 14.

    Fujioka, H.; Maehata, R.; Wakamatsu, S.; Nakahara, K.; Hayashi, T.; Oki, T. Org. Lett.2012, 14, 1054.

  15. 15.

    Zhao, S.; Wu, Y.; Sun, Q.; Cheng, T.-M.; Li, R.-T. Synthesis2015, 1154.

  16. 16.

    Huang, D.; Wang, H.; Xue, F.; Guan, H.; Li, L.; Peng, X.; Shi, Y. Org. Lett.2011, 13, 6350.

  17. 17.

    Doroski, T. A.; Cox, M. R.; Morgan, J. B. Tetrahedron Lett.2009, 50, 5162.

  18. 18.

    Ke, Z.; Tan, C. K.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc.2014, 136, 5627.

  19. 19.

    Hennecke, U.; Müller, C. H.; Fröhlich, R. Org. Lett.2011, 13, 860.

  20. 20.

    Denmark, S. E.; Burk, M. T. Org. Lett.2012, 14, 256.

  21. 21.

    (a) Kang, S. H.; Lee, S. B.; Park, C. M. J. Am. Chem. Soc.2003, 125, 15748. (b) Kang, S. H.; Kang, S. Y.; Park, C. M.; Kwon, H. Y.; Kim, M. Pure Appl. Chem.2005, 77, 1269.

  22. 22.

    Kwon, H. Y.; Park, C. M.; Lee, S. B.; Youn, J.-H.; Kang, S. H. Chem.–Eur. J.2008, 14, 1023.

  23. 23.

    Kang, S. H.; Park, C. M.; Lee, S. B.; Kim, M. Synlett2004, 1279.

  24. 24.

    Debnar, T.; Dreisigacker, S.; Menche, D. Chem. Commun.2013, 49, 725.

  25. 25.

    (a) Snyder, S. A.; Treitler, D. S.; Brucks, A. P. Aldrichimica Acta2011, 44, 27. (b) Murai, K.; Fujioka, H. Heterocycles2013, 87, 763.

  26. 26.

    (a) Denmark, S. E.; Kuester, W. E.; Burk, M. T. Angew. Chem., Int. Ed.2012, 51, 10938. (b) Tan, C. K.; Yeung, Y.-Y. Chem. Commun.2013, 49, 7985. (c) Cheng, Y. A.; Yu, W. Z.; Yeung, Y.-Y. Org. Biomol. Chem.2014, 12, 2333.

  27. 27.

    Fang, C.; Paull, D. H.; Hethcox, J. C.; Shugrue, C. R.; Martin, S. F. Org. Lett.2012, 14, 6290.

  28. 28.

    (a) Zhou, L.; Tan, C. K.; Jiang, X.; Chen, F.; Yeung, Y.-Y. J. Am. Chem. Soc.2010, 132, 15474. (b) Tan, C. K.; Le, C.; Yeung, Y.-Y. Chem. Commun.2012, 48, 5793. (c) Tan, C. K.; Er, J. C.; Yeung, Y.-Y. Tetrahedron Lett.2014, 55, 1243.

  29. 29.

    Chen, T.; Foo, T. J. Y.; Yeung, Y.-Y. ACS Catal.2015, 5, 4751.

  30. 30.

    Tungen, J. E.; Nolsøe, J. M. J.; Hansen, T. V. Org. Lett.2012, 14, 5884.

  31. 31.

    Ahmad, S. M.; Braddock, D. C.; Cansell, G.; Hermitage, S. A.; Redmond, J. M.; White, A. J. P. Tetrahedron Lett.2007, 48, 5948.

  32. 32.

    Ning, Z.; Jin, R.; Ding, J.; Gao, L. Synlett2009, 2291.

  33. 33.

    Denmark, S. E.; Burk, M. T. Proc. Natl. Acad. Sci. U. S. A.2010, 107, 20655.

  34. 34.

    Wilking, M.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Hennecke, U. J. Am. Chem. Soc.2013, 135, 8133.

  35. 35.

    Wong, Y.-C.; Yeung, Y.-Y. Org. Biomol. Chem.2016, 14, 3202.

  36. 36.

    Zhang, W.; Xu, H.; Xu, H.; Tang, W. J. Am. Chem. Soc.2009, 131, 3832.

  37. 37.

    Ma, S.; Lu, L. J. Org. Chem.2005, 70, 7629.

  38. 38.

    Khan, F. A.; Soma, L. Tetrahedron Lett.2007, 48, 85.

  39. 39.

    Colobert, F.; Castanet, A.-S.; Abillard, O. Eur. J. Org. Chem.2005, 3334.

  40. 40.

    Basu, P. K.; Ghosh, A. Org. Chem. Int.2012. Article ID 810476. https://doi.org/10.1155/2012/810476.

  41. 41.

    Gelat, F.; Lebrun, S.; Henry, N.; Agbossou-Niedercorn, F.; Michon, C.; Deniau, E. Synlett2017, 225.

  42. 42.

    Roehrs, J. A.; Pistoia, R. P.; Back, D. F.; Zeni, G. J. Org. Chem.2015, 80, 12470.

  43. 43.

    (a) Larock, R. C.; Yue, D. Tetrahedron Lett.2001, 42, 6011. (b) Yue, D.; Larock, R. C. J. Org. Chem.2002, 67, 1905.

  44. 44.

    (a) Agami, C.; Dechoux, L.; Hebbe, S. Synlett2001, 1440. b) Agami, C.; Dechoux, L.; Hamon, L.; Hebbe, S. Synthesis2003, 859.

  45. 45.

    Agami, C.; Dechoux, L.; Hebbe, S.; Moulinas, J. Synthesis2002, 79.

  46. 46.

    Andoh-Baidoo, R.; Danso, R.; Mukherjee, S.; Bandyopadhyay, D.; Banik, B. K. Heterocycl. Lett.2011, 1, 107.

  47. 47.

    Sai, M.; Matsubara, S. Org. Lett.2011, 13, 4676.

  48. 48.

    Zhou, L.; Chen, J.; Tan, C. K.; Yeung, Y.-Y. J. Am. Chem. Soc.2011, 133, 9164.

  49. 49.

    Márquez-Segovia, I.; Baeza, A.; Otero, A.; Nájera, C. Eur. J. Org. Chem.2013, 4962.

  50. 50.

    O'Broin, C. Q.; Fernández, P.; Martínez, C.; Muñiz, K. Org. Lett.2016, 18, 436.

  51. 51.

    Michael, F. E.; Sibbald, P. A.; Cochran, B. M. Org. Lett.2008, 10, 793.

  52. 52.

    Zhou, J.; Yeung, Y.-Y. Org. Biomol. Chem.2014, 12, 7482.

  53. 53.

    Prabagar, B.; Nayak, S.; Prasad, R.; Sahoo, A. K. Org. Lett.2016, 18, 3066.

  54. 54.

    Müller, C. H.; Fröhlich, R.; Daniliuc, C. G.; Hennecke, U. Org. Lett.2012, 14, 5944.

  55. 55.

    (a) Alcaide, B.; Almendros, P.; Luna, A.; Torres, M. R. Adv. Synth. Catal.2010, 352, 621. (b) Alcaide, B.; Almendros, P.; Luna, A.; Cembellín, S.; Arnó, M.; Domingo, L. R. Chem.– Eur. J.2011, 17, 11559.

  56. 56.

    He, Z.; Liu, W.; Li, Z. Chem. Asian J.2011, 6, 1340.

  57. 57.

    Kothandaraman, P.; Mothe, S. R.; Toh, S. S. M.; Chan, P. W. H. J. Org. Chem.2011, 76, 7633.

  58. 58.

    Kothandaraman, P.; Lauw, S. J. L.; Chan, P. W. H. Tetrahedron2013, 69, 7471.

  59. 59.

    Yan, Q.; Luo, J.; Zhang-Negrerie, D.; Li, H.; Qi, X.; Zhao, K. J. Org. Chem.2011, 76, 8690.

  60. 60.

    Kothandaraman, P.; Koh, B. Q.; Limpanuparb, T.; Hirao, H.; Chan, P. W. H. Chem.–Eur. J.2013, 19, 1978.

  61. 61.

    Li, Y.-L.; Li, J.; Ma, A.-L.; Huang, Y.-N.; Deng, J. J. Org. Chem.2015, 80, 3841.

  62. 62.

    Ma, C.; Xing, D.; Hu, W. Org. Lett.2016, 18, 3134.

  63. 63.

    Villuri, B. K.; Kotipalli, T.; Kavala, V.; Ichake, S. S.; Bandi, V.; Kuo, C.-W.; Yao, C.-F. RSC Adv.2016, 6, 74845.

  64. 64.

    Majumdar, K. C.; Kundu, U. K.; Das, U.; Jana, N. K.; Roy, B. Can. J. Chem.2005, 83, 63.

  65. 65.

    Bathula, S. R.; Reddy, M. P.; Viswanadham, K. K. D. R.; Sathyanarayana, P.; Reddy, M. S. Eur. J. Org. Chem.2013, 4552.

  66. 66.

    Zhou, W.; Xie, C.; Han, J.; Pan, Y. Org. Lett.2012, 14, 4766.

  67. 67.

    Panda, N.; Mothkuri, R. New J. Chem.2014, 38, 5727.

  68. 68.

    Dinda, M.; Samanta, S.; Eringathodi, S.; Ghosh, P. K. RSC Adv.2014, 4, 12252.

  69. 69.

    Wang, N.; Chen, B.; Ma, S. Adv. Synth. Catal.2014, 356, 485.

  70. 70.

    Hajra, S.; Bar, S.; Sinha, D.; Maji, B. J. Org. Chem.2008, 73, 4320.

  71. 71.

    Schwekendiek, K.; Glorius, F. Synthesis2006, 2996.

  72. 72.

    Rajesh, N.; Manisha, B.; Ranjith, J.; Krishna, P. R. RSC Adv.2016, 6, 6058.

  73. 73.

    Kawato, Y.; Kubota, A.; Ono, H.; Egami, H.; Hamashima, Y. Org. Lett.2015, 17, 1244.

  74. 74.

    Hu, Y.; Yi, R.; Wang, C.; Xin, X.; Wu, F.; Wan, B. J. Org. Chem.2014, 79, 3052.

  75. 75.

    Balaji, P. V.; Chandrasekaran, S. Chem. Commun.2014, 50, 70.

  76. 76.

    Huang, D.; Liu, X.; Li, L.; Cai, Y.; Liu, W.; Shi, Y. J. Am. Chem. Soc.2013, 135, 8101.

  77. 77.

    Crich, D.; Banerjee, A. J. Org. Chem.2006, 71, 7106.

  78. 78.

    Wang, X.; Xu, D.; Miao, C.; Zhang, Q.; Sun, W. Org. Biomol. Chem.2014, 12, 3108.

  79. 79.

    Li, H.; Widenhoefer, R. A. Tetrahedron2010, 66, 4827.

  80. 80.

    Agami, C.; Beauseigneur, A.; Comesse, S.; Dechoux, L. Tetrahedron Lett.2003, 44, 7667.

  81. 81.

    Hu, M.; He, X.; Niu, Z.; Yan, Z.; Zhou, F.; Shang, Y. Synthesis2014, 510.

  82. 82.

    Okitsu, T.; Sato, K.; Potewar, T. M.; Wada, A. J. Org. Chem.2011, 76, 3438.

  83. 83.

    Kiyani, H.; Kanaani, A.; Ajloo, D.; Ghorbani, F.; Vakili, M. Res. Chem. Intermed.2015, 41, 7739.

  84. 84.

    Kaewsri, W.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. RSC Adv.2016, 6, 48666.

  85. 85.

    Zhang, L.; Zeng, Q.; Mao, A.; Wu, Z.; Luo, T.; Xiao, Y.; Zhang, J. Org. Biomol. Chem.2014, 12, 8942.

  86. 86.

    Tripathi, C. B.; Mukherjee, S. Angew. Chem., Int. Ed.2013, 52, 8450.

  87. 87.

    Tripathi, C. B.; Mukherjee, S. Org. Lett.2015, 17, 4424.

  88. 88.

    Saber, A.; Driowya, M.; Alaoui, S.; Marzag, H.; Demange, L.; Álvarez, E.; Benhida, R.; Bougrin, K. Chem. Heterocycl. Compd.2016, 52, 31. [Khim. Geterotsikl. Soedin.2016, 52, 31.]

  89. 89.

    Lombardo, M.; Rispoli, G.; Licciulli, S.; Trombini, C.; Dhavale, D. D. Tetrahedron Lett.2005, 46, 3789.

  90. 90.

    Chen, C.; Andreani, T.; Li, H. Org. Lett.2011, 13, 6300.

  91. 91.

    Izumisawa, Y.; Togo, H. Green and Sustainable Chemistry2011, 1, 54.

  92. 92.

    Bodireddy, M. R.; Mohinuddin, P. M. K.; Gundala, T. R.; Reddy, N. C. G. Cogent Chem.2016, 2, 1154237.

  93. 93.

    Wagare, D. S.; Netankar, P. D.; Shaikh, M.; Farooqui, M.; Durrani, A. Environ. Chem. Lett.2017, 15, 475.

  94. 94.

    Zhao, R.; Gove, S.; Sundeen, J. E.; Chen, B.-C. Tetrahedron Lett.2001, 42, 2101.

  95. 95.

    Narender, M.; Reddy, M. S.; Kumar, V. P.; Srinivas, B.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Synthesis2007, 3469

  96. 96.

    Azizi, N.; Rahimi, Z.; Alipour, M. C. R. Chim.2015, 18, 626.

  97. 97.

    Madhav, B.; Murthy, S. N.; Anil Kumar, B. S. P.; Ramesh, K.; Nageswar, Y. V. D. Tetrahedron Lett.2012, 53, 3835.

  98. 98.

    Chen, X.-B.; Wang, X.-Q.; Song, J.-N.; Yang, Q.-L.; Huang, C.; Liu, W. Org. Biomol. Chem.2017, 15, 3611.

  99. 99.

    Nikpassand, M.; Fekri, L. Z.; Sanagou, S. Dyes Pigm.2017, 136, 140.

  100. 100.

    Xu, F.; Chen, Y.; Fan, E.; Sun, Z. Org. Lett.2016, 18, 2777.

  101. 101.

    Moghaddam, F. M.; Zargarani, D. J. Sulfur Chem.2009, 30, 507.

  102. 102.

    Okitsu, T.; Sato, K.; Wada, A. Org. Lett.2010, 12, 3506.

  103. 103.

    Hu, X.-Q.; Chen, J.-R.; Wei, Q.; Liu, F.-L.; Deng, Q.-H.; Zou, Y.-Q.; Xiao, W.-J. Eur. J. Org. Chem.2014, 3082.

  104. 104.

    Maleki, B.; Ashrafi, S. S. J. Mex. Chem. Soc.2014, 58, 76.

  105. 105.

    Zhou, L.; Zhou, J.; Tan, C. K.; Chen, J.; Yeung, Y.-Y. Org. Lett.2011, 13, 2448.

  106. 106.

    Zhou, L.; Chen, J.; Zhou, J.; Yeung, Y.-Y. Org. Lett.2011, 13, 5804.

  107. 107.

    (a) Fujioka, H.; Murai, K.; Ohba, Y.; Hiramatsu, A.; Kita, Y. Tetrahedron Lett.2005, 46, 2197.(b) Fujioka, H.; Murai, K. Kubo, O.; Ohba, Y.; Kita, Y. Tetrahedron2007, 63, 638.

  108. 108.

    Sant' Anna, G. S.; Machado, P.; Sauzem, P. D.; Rosa, F. A.; Rubin, M. A.; Ferreira, J.; Bonacorso, H. G.; Zanatta, N.; Martins, M. A. P. Bioorg. Med. Chem. Lett.2009, 19, 546.

  109. 109.

    Braddock, D. C.; Cailleau, T.; Cansell, G.; Hermitage, S. A.; Pouwer, R. H.; Redmond, J. M.; White, A. J. P. Tetrahedron: Asymmetry2010, 21, 2911.

  110. 110.

    Timmons, C.; Chen, D.; Xu, X.; Li, G. Eur. J. Org. Chem.2003, 3850.

  111. 111.

    Daswani, U.; Dubey, N.; Sharma, P.; Kumar, A. New J. Chem.2016, 40, 8093.

  112. 112.

    Kamal, A.; Chouhan, G.; Ahmed, K. Tetrahedron Lett.2002, 43, 6947.

  113. 113.

    Pardeshi, S. P.; Patil, S. S.; Bobade, V. D. Synth. Commun.2010, 40, 1601.

  114. 114.

    Borsoi, A. F.; Coldeira, M. E.; Pissinate, K.; Macchi, F. S.; Basso, L. A.; Santos, D. S.; Machado, P. Synth. Commun.2017, 47, 1319.

  115. 115.

    Li, L.; Zhang, G.; Zhu, A.; Zhang, L. J. Org. Chem.2008, 73, 3630.

  116. 116.

    Hajra, S.; Sinha, D.; Bhowmick, M. J. Org. Chem.2007, 72, 1852.

  117. 117.

    Hu, Y.; Yi, R.; Yu, X.; Xin, X.; Wang, C.; Wan, B. Chem. Commun.2015, 51, 15398.

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Correspondence to Olga V. Hordiyenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 1–29

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Lyubchuk, T.V., Hordiyenko, O.V. The use of N-halosuccinimides for cyclization with the formation of five-membered heterocyclic compounds. Chem Heterocycl Comp (2020). https://doi.org/10.1007/s10593-020-02616-5

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Keywords

  • N-halosuccinimide
  • cyclization
  • five-membered heterocycle
  • halolactonization