Citation: Yang Kai, Yao Chen, Gao Juanjuan, Chen Sihong, Zheng Xuejie, Deng Luxuan, Zhang Yu'na, Liu Meijuan, Wang Zhaoyang. Progress on the Synthesis of Pyrido[1, 2-a]benzimidazoles[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4168-4183. doi: 10.6023/cjoc202005074 shu

Progress on the Synthesis of Pyrido[1, 2-a]benzimidazoles

Yang Kai ^a,b,, ,
Yao Chen ^b ,
Gao Juanjuan ^c ,
Chen Sihong ^b ,
Zheng Xuejie ^b ,
Deng Luxuan ^b ,
Zhang Yu'na ^b ,
Liu Meijuan ^b ,
Wang Zhaoyang ^b,,

a.
College of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000
b.
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry, South China Normal University, Guangzhou 510006
c.
College of Sports and Rehabilitation, Gannan Medical University, Ganzhou, Jiangxi 341000

Corresponding author: Yang Kai, kai_yangyang@126.com Wang Zhaoyang, wangzy@scnu.edu.cn
Received Date: 27 May 2020
Revised Date: 15 June 2020
Available Online: 30 June 2020
Fund Project: the Undergraduates Innovation Project of South China Normal University 202003Project supported by the Guangdong Provincial Science and Technology Project (No. 2017A010103016), the Scientific Research Project of Gannan Medical University (No. YB201903), the Undergraduates Innovation Project of South China Normal University (No. 202003) and the Extracurricular Project for Students' Scientific Research of South China Normal University (No.19HHGB08)the Extracurricular Project for Students' Scientific Research of South China Normal University 19HHGB08the Guangdong Provincial Science and Technology Project 2017A010103016the Scientific Research Project of Gannan Medical University YB201903

Figures(24)

Pyrido[1, 2-a]benzimidazole is one of the important azaheterocycles with three fused aromatic rings. These molecules containing this skeleton have wide application prospects in the fields of medicinal chemistry and materials, and their syntheses have attracted much attention in organic chemistry. According to the retrosynthetic analysis on the construction of different rings in target molecules, the research progress on the synthesis of pyrido[1, 2-a]benzimidazoles from different types of starting materials is reviewed, and its future development direction is prospected.
- azaheterocycle,
- pyrido[1, 2-a]benzimidazole,
- retrosynthetic analysis,
- metal catalysis,
- C-H activation,
- tandem reaction,
- 2-aminopyridine,
- o-phenylenediamine
1. [1]
  Stepien, M.; Gonka, E.; Zyla, M.; Sprutta, N. Chem. Rev. 2017, 117, 3479. doi: 10.1021/acs.chemrev.6b00076
2. [2]
  Tan, J.-F.; Bormann, C. T.; Perrin, F. G.; Chadwick, F. M.; Seyerin, K.; Cramer, N. J. Am. Chem. Soc. 2019, 141, 10372. doi: 10.1021/jacs.9b04111
3. [3]
  Gomha, S. M.; Eldebss, T. M. A.; Badrey, M. G.; Abdulla, M. M.; Mayhoub, A. S. Chem. Biol. Drug Des. 2015, 86, 1292. doi: 10.1111/cbdd.12593
4. [4]
  Xie, Y.-J.; Wu, J.; Che, X.-Z.; Chen, Y.; Huang, H.-W.; Deng, G.-J. Green Chem. 2016, 18, 667. doi: 10.1039/C5GC01978H
5. [5]
  Perin, N.; Bobanovic, K.; Zlatar, I.; Jelic, D.; Kelava, V.; Kostrun, S.; Markovic, V. G.; Brajsa, K.; Hranjec, M. Eur. J. Med. Chem. 2017, 125, 722. doi: 10.1016/j.ejmech.2016.09.084
6. [6]
  Jovanovic, I. N.; Jadresko, D.; Milicevic, A.; Hranjec, M.; Perin, N. Electrochim. Acta 2019, 297, 452. doi: 10.1016/j.electacta.2018.11.198
7. [7]
  Okombo, J.; Brunschwig, C.; Singh, K.; Dziwornu, G. A.; Barnard, L.; Njoroge, M.; Wittlin, S.; Chibale, K. ACS Infect. Dis. 2019, 5, 372. doi: 10.1021/acsinfecdis.8b00279
8. [8]
  Mayoka, G.; Njoroge, M.; Okombo, J.; Gibhard, L.; Sanches-Vaz, M.; Fontinha, D.; Birkholtz, L. M.; Reader, J.; van der Watt, M.; Coetzer, T. L.; Lauterbach, S.; Churchyard, A.; Bezuidenhout, B.; Egan, T. J.; Yeates, C.; Wittlin, S.; Prudencio, M.; Chibale, K. J. Med. Chem. 2019, 62, 1022. doi: 10.1021/acs.jmedchem.8b01769
9. [9]
  Takeshita, H.; Watanabe, J.; Kimura, Y.; Kawakami, K.; Takahashi, H.; Takemura, M.; Kitamura, A.; Someya, K.; Nakajima, R. Bioorg. Med. Chem. Lett. 2010, 20, 3893. doi: 10.1016/j.bmcl.2010.05.024
10. [10]
  Okombo, J.; Singh, K.; Mayoka, G.; Ndubi, F.; Barnard, L.; Njogu, P. M.; Njoroge, M.; Gibhard, L.; Brunschwig, C.; Vargas, M.; Keiser, J.; Egan, T. J.; Chibale, K. ACS Infect. Dis. 2017, 3, 411. doi: 10.1021/acsinfecdis.6b00205
11. [11]
  Chalmers, B. A.; Saha, S.; Nguyen, T.; McMurtrie, J.; Sigurdsson, S. T.; Bottle, S. E.; Masters, K. S. Org. Lett. 2014, 16, 5528. doi: 10.1021/ol502003a
12. [12]
  Karak, P.; Dutta, C.; Dutta, T.; Koner, A. L.; Choudhury, J. Chem. Commun. 2019, 55, 6791. doi: 10.1039/C9CC02710F
13. [13]
  Pericherla, K.; Kaswan, P.; Pandey, K.; Kumar, A. Synthesis 2015, 47, 887. doi: 10.1055/s-0034-1380182
14. [14]
  Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. 2015, 51, 1555. doi: 10.1039/C4CC08495K
15. [15]
  Zhao, X.-Y.; Ding, Y.-Y.; Lu, Y.-T.; Kang, C.-M. Chin. J. Org. Chem. 2019, 39, 1304(in Chinese).
16. [16]
  Khajuria, R.; Rasheed, S.; Khajuria, C.; Kapoor, K. K.; Das, P. Synthesis 2018, 50, 2131. doi: 10.1055/s-0036-1589533
17. [17]
  Ahneman, D. T.; Estrada, J. G.; Lin, S. S.; Dreher, S. D.; Doyle, A. G. Science 2018, 360, 186. doi: 10.1126/science.aar5169
18. [18]
19. [19]
  Abrams, R.; Lefebvre, Q.; Clayden, J. Angew. Chem., Int. Ed. 2018, 57, 13587. doi: 10.1002/anie.201809323
20. [20]
  Venkatesh, C.; Sundaram, G. S. M.; Ila, H.; Junjappa, H. J. Org. Chem. 2006, 71, 1280. doi: 10.1021/jo0522411
21. [21]
  Liubchak, K.; Nazarenko, K.; Tolmachev, A. Tetrahedron 2012, 68, 2993. doi: 10.1016/j.tet.2012.02.027
22. [22]
  Chen, F.; Chen, H.; Wu, Q.-A.; Luo, S.-P. Chin. J. Org. Chem. 2020, 40, 339(in Chinese).
23. [23]
  Barolo, S. M.; Wang, Y.; Rossi, R. A.; Cuny, G. D. Tetrahedron 2013, 69, 5487. doi: 10.1016/j.tet.2013.04.087
24. [24]
  Wang, H.-G.; Wang, Y.; Peng, C.-L.; Zhang, J.-C.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217. doi: 10.1021/ja1067993
25. [25]
  Masters, K. S.; Rauws, T. R. M.; Yadav, A. K.; Herrebout, W. A.; Van der Veken, B.; Maes, B. U. W. Chem.-Eur. J. 2011, 17, 6315. doi: 10.1002/chem.201100574
26. [26]
  Wu, Y.-X.; Xi, Y.-C.; Zhao, M.; Wang, S.-Y. Chin. J. Org. Chem. 2018, 38, 2590(in Chinese).
27. [27]
28. [28]
  Duan, Z.-L.; Zhang, L.; Zhang, W.-X.; Lu, L.-J.; Zeng, L.; Shi, R.-Y.; Lei, A.-W. ACS Catal. 2020, 10, 3828. doi: 10.1021/acscatal.0c00103
29. [29]
  Lv, S.-D.; Han, X.-X.; Wang, J.-Y.; Zhou, M.-Y.; Wu, Y.-W.; Ma, L.; Niu, L.-W.; Gao, W.; Zhou, J.-H.; Hu, W.; Cui, Y.-Z.; Chen, J.-B. Angew. Chem., Int. Ed. 2020, 59, 11573. doi: 10.1002/anie.202003502
30. [30]
  Xue, F.-L.; Peng, P.; Shi, J.; Zhong, M.-L.; Wang, Z.-Y. Synth. Commun. 2014, 44, 1944. doi: 10.1080/00397911.2013.879899
31. [31]
  Rao, D. N.; Rasheed, S.; Vishwakarma, R. A.; Das, P. RSC Adv. 2014, 4, 25600. doi: 10.1039/C4RA02279C
32. [32]
  Kutsumura, N.; Kunimatsu, S.; Kagawa, K.; Otani, T.; Saito, T. Synthesis 2011, 3235.
33. [33]
  Qian, G.-Y.; Liu, B.-X.; Tan, Q.-T.; Zhang, S.-W.; Xu, B. Eur. J. Org. Chem. 2014, 4837.
34. [34]
  He, Y.-M.; Huang, J.-B.; Liang, D.-D.; Liu, L.-Y.; Zhu, Q. Chem. Commun. 2013, 49, 7352. doi: 10.1039/c3cc43784a
35. [35]
  Liang, D.-D.; He, Y.-M.; Liu, L.-Y.; Zhu, Q. Org. Lett. 2013, 15, 3476. doi: 10.1021/ol4015656
36. [36]
  Lv, Z.-G.; Liu, J.; Wei, W.; Wu, J.; Yu, W.-Q.; Chang, J.-B. Adv. Synth. Catal. 2016, 358, 2759. doi: 10.1002/adsc.201600455
37. [37]
  Lee, H. E.; Lee, M. J.; Park, J. K. Asian J. Org. Chem. 2019, 8, 1659. doi: 10.1002/ajoc.201900347
38. [38]
  Xu, C.-R.; Wang, K.-X.; Li, D.-W.; Lin, L.-L.; Feng, X.-M. Angew. Chem., Int. Ed. 2019, 58, 18438. doi: 10.1002/anie.201910898
39. [39]
  (a) Maiti, D.; Fors, B. P; Henderson, J. L.; Nakamura, Y.; Buchwald, S. L. Chem. Sci. 2011, 2, 57.
  (b) Han, Y.; Zhang, M.; Zhang, Y.-Q.; Zhang, Z.-H. Green Chem. 2018, 20, 4891.
40. [40]
  Wexler, R. P.; Nuhant, P.; Senter, T. J.; Gale-Day, Z. J. Org. Lett. 2019, 21, 4540. doi: 10.1021/acs.orglett.9b01434
41. [41]
  Rasheed, S.; Rao, D. N.; Das, P. J. Org. Chem. 2015, 80, 9321. doi: 10.1021/acs.joc.5b01396
42. [42]
  Yan, H.; Guo, H.; Zhou, X.-Q.; Zuo, Z.-Y.; Liu, J.-L.; Zhang, G.-H.; Zhang, S. Synlett 2019, 30, 1469. doi: 10.1055/s-0037-1611847
43. [43]
  (a) Louillat, M. L.; Patureau, F. W. Chem. Soc. Rev. 2014, 43, 901.
  (b) Li, L.-X.; Li, Y.; Zhao, Z.-G.; Luo, H.-T.; Ma, Y.-N. Org. Lett. 2019, 21, 5995.
  (c) Matsumoto, M.; Wada, K.; Urakawa, K.; Ishikawa, H. Org. Lett. 2020, 22, 781.
44. [44]
  Manna, S.; Matcha, K.; Antonchick, A. P. Angew. Chem., Int. Ed. 2014, 53, 8163. doi: 10.1002/anie.201403712
45. [45]
  Liu, X.-L.; Chen, J.; Ma, T.-L. Org. Biomol. Chem. 2018, 16, 8662. doi: 10.1039/C8OB02351D
46. [46]
  Xie, Y.-J.; Wu, J.; Che, X.-Z.; Chen, Y.; Huang, H.-W.; Deng, G.-J. Green Chem. 2016, 18, 667. doi: 10.1039/C5GC01978H
47. [47]
  Zhang, W.-W.; Li, H.-J.; Wang, M.-R.; Wang, L.-J.; Zhang, A.-H.; Wu, Y.-C. New J. Chem. 2019, 43, 413. doi: 10.1039/C8NJ04028A
48. [48]
  Wu, Z.-Q.; Huang, Q.; Zhou, X.-G.; Yu, L.-T.; Li, Z.-K.; Wu, D. Eur. J. Org. Chem. 2011, 5242.
49. [49]
  Yang, K.; Wang, Z.-Y.; Fu, J.-H.; Tan, Y.-H. Prog. Chem. 2010, 22, 2126(in Chinese).
50. [50]
  Cai, Q.; Li, Z. Q.; Wei, J. J.; Fu, L. B.; Ha, C. Y.; Pei, D. Q.; Ding, K. Org. Lett. 2010, 12, 1500. doi: 10.1021/ol1002225
51. [51]
  Zhou, B.-W.; Gao, J.-R.; Jiang, D.; Jia, J.-H.; Yang, Z.-P.; Jin, H.-W. Synthesis 2010, 2794.
52. [52]
53. [53]
  Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2016, 45, 6888. doi: 10.1039/C6CS90108E
54. [54]
  Nagesh, H. N.; Suresh, A.; Reddy, M. N.; Suresh, N.; Subbalakshmi, J.; Sekhar, K. V. G. C. RSC Adv. 2016, 6, 15884. doi: 10.1039/C5RA24048D
55. [55]
  Kato, J.; Ito, Y.; Ijuin, R.; Aoyama, H.; Yokomatsu, T. Org. Lett. 2013, 15, 3794. doi: 10.1021/ol4017723
56. [56]
  da Silva, R. B.; Coelho, F. L.; Rodembusch, F. S.; Schwab, R. S.; Schneider, J. M. F. M.; Rampon, D. D.; Schneider, P. H. New J. Chem. 2019, 43, 11596. doi: 10.1039/C9NJ01948K
57. [57]
  Yin, C.-X.; Huo, F.-J.; Cooley, N. P.; Spencer, D.; Bartholomew, K.; Barnes, C. L.; Glass, T. E. ACS Chem. Neurosci. 2017, 8, 1159. doi: 10.1021/acschemneuro.6b00420
58. [58]
  Panda, K.; Suresh, J. R.; Ila, H.; Junjappa, H. J. Org. Chem. 2003, 68, 3498. doi: 10.1021/jo026786w
59. [59]
  Kotovskaya, S. K.; Baskakova, Z. M.; Charushin, V. N.; Chupakhin, O. N.; Belanov, E. F.; Bormotov, N. I.; Balakhnin, S. M.; Serova. O. A. Pharm. Chem. J. 2005, 39, 574. doi: 10.1007/s11094-006-0023-9
60. [60]
  Shaaban, M. R.; Eldebss, T. M. A.; Darweesh, A. F.; Farag, A. M. J. Heterocycl. Chem. 2008, 45, 1739. doi: 10.1002/jhet.5570450627
61. [61]
  Ibrahim, M. A. Tetrahedron 2013, 69, 6861. doi: 10.1016/j.tet.2013.06.011
62. [62]
  Goli-Garmroodi, F.; Omidi, M.; Saeedi, M.; Sarrafzadeh, F.; Rafinejad, A.; Mahdavi, M.; Bardajee, G. R.; Akbarzadeh, T.; Firoozpour, L.; Shafiee, A.; Foroumadi, A. Tetrahedron Lett. 2015, 56, 743. doi: 10.1016/j.tetlet.2014.12.099
63. [63]
  Tireli, M.; Starcevic, K.; Martinovic, T.; Pavelic, S. K.; Karminski-Zamola, G.; Hranjec, M. Mol. Diversity 2017, 21, 201. doi: 10.1007/s11030-016-9702-y
64. [64]
  Vodolazhenko, M. A.; Mykhailenko, A. E.; Gorobets, N. Y.; Desenko, S. M. J. Heterocycl. Chem. 2017, 54, 753. doi: 10.1002/jhet.2617
65. [65]
  Lyons, D. M.; Huttunen, K. M.; Browne, K. A.; Ciccone, A.; Trapani, J. A.; Denny, W. A.; Spicer, J. A. Bioorg. Med. Chem. 2011, 19, 4091. doi: 10.1016/j.bmc.2011.05.013
66. [66]
  Jardosh, H. H.; Sangani, C. B.; Patel, M. P.; Patel, R. G. Chin. Chem. Lett. 2013, 24, 123. doi: 10.1016/j.cclet.2013.01.021
67. [67]
  Teng, Q.-H.; Peng, X.-J.; Mo, Z.-Y.; Xu, Y.-L.; Tang, H.-T.; Wang, H.-S.; Sun, H.-B.; Pan, Y.-M. Green Chem. 2018, 20, 2007. doi: 10.1039/C8GC00069G
68. [68]
  Jiang, Z.-Q.; Miao, D. Z.; Tong, Y.; Pan, Q.; Li, X.-T.; Hu, R.-H.; Han, S.-Q. Synthesis 2015, 47, 1913. doi: 10.1055/s-0034-1380506
69. [69]
  Ge, Y.-Q.; Jia, J.; Yang, H.; Tao, X.-T.; Wang, J.-W. Dyes Pigm. 2011, 88, 344. doi: 10.1016/j.dyepig.2010.08.005
70. [70]
  Yang, H.; Ge, Y.-Q.; Jia, J.; Wang, J.-W. J. Lumin. 2011, 131, 749. doi: 10.1016/j.jlumin.2010.11.030
71. [71]
  Peng, J.-S.; Shang, G.-N.; Chen, C.-X.; Miao, Z.-S.; Li, B. J. Org. Chem. 2013, 78, 1242. doi: 10.1021/jo302471z
72. [72]
  Zheng, L.-Y.; Hua, R.-M. J. Org. Chem. 2014, 79, 3930. doi: 10.1021/jo500401n
73. [73]
  Ghosh, K.; Nishii, Y.; Miura, M. ACS Catal. 2019, 9, 11455. doi: 10.1021/acscatal.9b04254
74. [74]
  Mai, S.-Y.; Luo, Y.-X.; Huang, X.-Y.; Shu, Z.-H.; Li, B.-N.; Lan, Y.; Song, Q.-L. Chem. Commun. 2018, 54, 10240. doi: 10.1039/C8CC05390A
75. [75]
  Miao, W.-Q.; Liu, J.-Q.; Wang, X.-S. Org. Biomol. Chem. 2017, 15, 5325. doi: 10.1039/C7OB01022B
76. [76]
  Liu, J.-M.; Zhang, N.-F.; Yue, Y.-Y.; Liu, G.-H.; Liu, R.; Zhang, Y.-L.; Zhuo, K.-L. Eur. J. Org. Chem. 2013, 7683.
77. [77]
  Yan, L.-P.; Zhao, D.-B.; Lan, J.-B.; Cheng, Y.-Y.; Guo, Q.; Li, X.-Y.; Wu, N.-J.; You, J.-S. Org. Biomol. Chem. 2013, 11, 7966. doi: 10.1039/c3ob41760c
78. [78]
  Chen, C.-X.; Shang, G.-N.; Zhou, J.-J.; Yu, Y.-H.; Li, B.; Peng, J.-S. Org. Lett. 2014, 16, 1872. doi: 10.1021/ol500248h
79. [79]
  Zhao, G.-Y.; Chen, C.-X.; Yue, Y.-X.; Yu, Y.-H.; Peng, J.-S. J. Org. Chem. 2015, 80, 2827. doi: 10.1021/jo502632b
80. [80]
  Li, X.; Chen, X.; Wang, H.; Chen, C.-X.; Sun, P.; Mo, B.-C.; Peng, J.-S. Org. Biomol. Chem. 2019, 17, 4014. doi: 10.1039/C9OB00482C
81. [81]
  Bera, S. K.; Alam, M. T.; Mal, P. J. Org. Chem. 2019, 84, 12009. doi: 10.1021/acs.joc.9b01921
82. [82]
  Wezeman, T.; Scopelliti, R.; Tirani, F. F.; Severin, K. Adv. Synth. Catal. 2019, 361, 1383. doi: 10.1002/adsc.201801341
83. [83]
  Huang, J.-R.; Dong, L.; Han, B.; Peng, C.; Chen, Y.-C. Chem.-Eur. J. 2012, 18, 8896. doi: 10.1002/chem.201201207
84. [84]
  Dong, L.; Huang, J.-R.; Qu, C.-H.; Zhang, Q.-R.; Zhang, W.; Han, B.; Peng, C. Org. Biomol. Chem. 2013, 11, 6142. doi: 10.1039/c3ob41177j
85. [85]
  Ghorai, D.; Choudhury, J. Chem. Commun. 2014, 50, 15159. doi: 10.1039/C4CC07170K
86. [86]
  Thenarukandiyil, R.; Dutta, C.; Choudhury, J. Chem.-Eur. J. 2017, 23, 15529. doi: 10.1002/chem.201703687
87. [87]
  Morioka, R.; Nobushige, K.; Satoh, T.; Hirano, K.; Miura, M. Org. Lett. 2015, 17, 3130. doi: 10.1021/acs.orglett.5b01452
88. [88]
  Reddy, V. P.; Iwasaki, T.; Kambe, N. Org. Biomol. Chem. 2013, 11, 2249. doi: 10.1039/c3ob27396b
89. [89]
  Sun, M.-M.; Wu, H.-D.; Zheng, J.-N.; Bao, W.-L. Adv. Synth. Catal. 2012, 354, 835. doi: 10.1002/adsc.201100801
90. [90]
  Chen, L.; Zhang, X.; Chen, B.; Li, B.; Li, Y.-B. Chem. Heterocycl. Compd. 2017, 53, 618. doi: 10.1007/s10593-017-2101-1
91. [91]
  Reddy, C. R.; Burra, A. G. J. Org. Chem. 2019, 84, 9169. doi: 10.1021/acs.joc.9b01118
92. [92]
  Peng, H.-B.; Yu, J.-T.; Jiang, Y.; Wang, L.; Cheng, J. Org. Biomol. Chem. 2015, 13, 5354. doi: 10.1039/C5OB00450K
93. [93]
  Li, P.-Y.; Zhang, X.-Y.; Fan, X.-S. J. Org. Chem. 2015, 80, 7508. doi: 10.1021/acs.joc.5b01092
94. [94]
  Qi, Z.-S.; Yu, S.-J.; Li, X.-W. J. Org. Chem. 2015, 80, 3471. doi: 10.1021/acs.joc.5b00059
95. [95]
  Xue, C.-W.; Han, J.-W.; Zhao, M.; Wang, L.-M. Org. Lett. 2019, 21, 4402. doi: 10.1021/acs.orglett.9b00761
96. [96]
97. [97]
98. [98]
  Milisiunaite, V.; Arbaciauskiene, E.; Bieliauskas, A.; Vilkauskaite, G.; Sackus, A.; Holzer, W. Tetrahedron 2015, 71, 3385. doi: 10.1016/j.tet.2015.03.092
99. [99]
  Rustagi, V.; Aggarwal, T.; Verma, A. K. Green Chem. 2011, 13, 1640. doi: 10.1039/c1gc15346c
100. [100]
  Rustagi, V.; Tiwari, R.; Verma, A. K. Eur. J. Org. Chem. 2012, 4590.
101. [101]
  Ouyang, H.-C.; Tang, R.-Y.; Zhong, P.; Zhang, X.-G.; Li, J.-H. J. Org. Chem. 2011, 76, 223. doi: 10.1021/jo102060j
102. [102]
  Gvozdev, V. D.; Shavrin, K. N.; Baskir, E. G.; Egorov, M. P.; Nefedov, O. M. Mendeleev Commun. 2017, 27, 231. doi: 10.1016/j.mencom.2017.05.004
103. [103]
  Chaitanya, T. K.; Prakash, K. S.; Nagarajan, R. Tetrahedron 2011, 67, 6934. doi: 10.1016/j.tet.2011.06.076
104. [104]
  Mishra, M.; Twardy, D.; Ellstrom, C.; Wheeler, K. A.; Dembinski, R.; Török, B. Green Chem. 2019, 21, 99. doi: 10.1039/C8GC02520G
105. [105]
  Adib, M.; Zainali, M.; Kim, I. Synlett 2016, 27, 1844. doi: 10.1055/s-0035-1561939
106. [106]
  Yan, C.-G.; Wang, Q.-F.; Song, X.-K.; Sun, J. J. Org. Chem. 2009, 74, 710. doi: 10.1021/jo802166t
107. [107]
  Hu, Y.; Wang, T.; Liu, Y.-Z.; Nie, R.-F.; Yang, N.-H.; Wang, Q.-T.; Li, G.-B.; Wu, Y. Org. Lett. 2020, 22, 501. doi: 10.1021/acs.orglett.9b04256
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6. [6]
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