Copyright (c) 2022 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
C-H Functionalization and C-N Bond Formation Approaches under Catalytic Conditions for the Synthesis of α-Ketoamides and 2,4-Disubstituted-1,3,5-triazines
Corresponding Author(s) : Chandi C. Malakar
Asian Journal of Chemistry,
Vol. 34 No. 7 (2022): Vol 34 Issue 7, 2022
Abstract
This work describes an easy way to perform approach for the transformation of arylmethyl ketones to α-ketoamides using secondary amines as starting materials in the presence of iodine as a catalyst in water under peroxide free reaction conditions. The established amidation reaction proceeds via α-C(sp3)-H functionalization and C-N bond formation approaches in water at ambient temperature. On the other hand, a novel and straightforward synthesis of 2,4-disubstituted-1,3,5-triazines via nickel-catalyzed cyclization of amidines with DMSO as one-carbon synthon has been developed. The developed strategy proceeds via C-N bond formation.
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- H.B. Deng, J.K. Jung, T. Liu, K.W. Kuntz, M.L. Snapper and A.H. Hoveyda, J. Am. Chem. Soc., 125, 9032 (2003); https://doi.org/10.1021/ja030249r
- G.G. Xu and F.A. Etzkorn, Org. Lett., 12, 696 (2010); https://doi.org/10.1021/ol9027013
- Z. Li, A.C. Ortega-Vilain, G.S. Patil, D.L. Chu, J.E. Foreman, D.D. Eveleth and J.C. Powers, J. Med. Chem., 39, 4089 (1996); https://doi.org/10.1021/jm950541c
- S. Chatterjee, D. Dunn, M. Tao, G. Wells, Z.-Q. Gu, R. Bihovsky, M.A. Ator, R. Siman and J.P. Mallamo, Bioorg. Med. Chem. Lett., 9, 2371 (1999); https://doi.org/10.1016/S0960-894X(99)00392-3
- M.M. Sheha, N.M. Mahfouz, H.Y. Hassan, A.F. Youssef, T. Mimoto and Y. Kiso, Eur. J. Med. Chem., 35, 887 (2000); https://doi.org/10.1016/S0223-5234(00)00187-2
- Y.H. Chen, Y.H. Zhang, H.J. Zhang, D.Z. Liu, M. Gu, J.Y. Li, F. Wu, X.Z. Zhu, J. Li and F.J. Nan, J. Med. Chem., 49, 1613 (2006); https://doi.org/10.1021/jm050896o
- K. Ni, L.G. Meng, K. Wang and L. Wang, Org. Lett., 20, 2245 (2018); https://doi.org/10.1021/acs.orglett.8b00586
- D. Kumar, S.R. Vemula and G.R. Cook, ACS Catal., 6, 4920 (2016); https://doi.org/10.1021/acscatal.6b01116
- C. De Risi, G.P. Pollini and V. Zanirato, Chem. Rev., 116, 3241 (2016); https://doi.org/10.1021/acs.chemrev.5b00443
- K.K.S. Sai, P.A. Esteves, E.T. da Penha and D.A. Klumpp, J. Org. Chem., 73, 6506 (2008); https://doi.org/10.1021/jo801208m
- Z. Zhang, Q. Zhang, Z. Ni and Q. Liu, Chem. Commun., 46, 1269 (2010); https://doi.org/10.1039/b917856b
- H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto and T. Taga, J. Am. Chem. Soc., 109, 5031 (1987); https://doi.org/10.1021/ja00250a050
- N. Fusetani, S. Matsunaga, H. Matsumoto and Y. Takebayashi, J. Am. Chem. Soc., 112, 7053 (1990); https://doi.org/10.1021/ja00175a045
- C. Dugave, Curr. Org. Chem., 6, 1397 (2002); https://doi.org/10.2174/1385272023373301
- X.J. Wang and F.A. Etzkorn, Biopolymers, 84, 125 (2006); https://doi.org/10.1002/bip.20240
- H.H. Wasserman and A.K. Petersen, J. Org. Chem., 62, 8972 (1997); https://doi.org/10.1021/jo9718253
- T. Higuchi, S. Uzu and M. Hirobe, J. Am. Chem. Soc., 112, 7051 (1990); https://doi.org/10.1021/ja00175a044
- C.K. Liu, Z. Fang, Z. Yang, Q.W. Li, S.Y. Guo and K. Guo, RSC Adv., 6, 25167 (2016); https://doi.org/10.1039/C5RA27653E
- U. Sharma, R. Sharma, R. Kumar, I. Kumar and B. Singh, Synthesis, 47, 2347 (2015); https://doi.org/10.1055/s-0034-1380435
- R. Deshidi, S. Devari and B.A. Shah, Eur. J. Org. Chem., 1428 (2015); https://doi.org/10.1002/ejoc.201403547
- S. Dutta, S.S. Kotha and G. Sekar, RSC Adv., 5, 47265 (2015); https://doi.org/10.1039/C5RA05671C
- S.S. Kotha, S. Chandrasekar, S. Sahu and G. Sekar, Eur. J. Org. Chem., 7451 (2014); https://doi.org/10.1002/ejoc.201402961
- S.S. Kotha and G. Sekar, Tetrahedron Lett., 56, 6323 (2015); https://doi.org/10.1016/j.tetlet.2015.09.053.
- F.T. Du and J.X. Ji, Chem. Sci., 3, 460 (2012); https://doi.org/10.1039/C1SC00312G
- W. Wei, Y. Shao, H.Y. Hu, F. Zhang, C. Zhang, Y. Xu and X.B. Wan, J. Org. Chem., 77, 7157 (2012); https://doi.org/10.1021/jo301117b
- F. Liu, K. Zhang, Y. Liu, S. Chen, Y. Chen, D. Zhang, C. Lin and B. Wang, RSC Adv., 7, 7158 (2017); https://doi.org/10.1039/C6RA26679G
- B. Du, B. Jin and P. Sun, Org. Biomol. Chem., 12, 4586 (2014); https://doi.org/10.1039/C4OB00520A
- M. Ramanathan, C. Kuo and K.S.T. Liu, Org. Biomol. Chem., 14, 11446 (2016); https://doi.org/10.1039/C6OB02361D
- N. Mupparapu, S. Khan, S. Battula, M. Kushwaha, A.P. Gupta, Q.N. Ahmed and R.A. Vishwakarma, Org. Lett., 16, 1152 (2014); https://doi.org/10.1021/ol5000204
- C. Zhang, X.L. Zong, L.R. Zhang and N. Jiao, Org. Lett., 14, 3280 (2012); https://doi.org/10.1021/ol301130u
- C. Zhang and N. Jiao, J. Am. Chem. Soc., 132, 28 (2010); https://doi.org/10.1021/ja908911n
- R. Deshidi, M. Kumar, S. Devari and B.A. Shah, Chem. Commun., 50, 9533 (2014); https://doi.org/10.1039/C4CC03783A
- M. Kumar, S. Devari, A. Kumar, S. Sultan, Q.N. Ahmed, M. Rizvi and B.A. Shah, Asian J. Org. Chem., 4, 438 (2015); https://doi.org/10.1002/ajoc.201500022
- C. Zhang, Z.J. Xu, L.R. Zhang and N. Jiao, Angew. Chem. Int. Ed., 50, 11088 (2011); https://doi.org/10.1002/anie.201105285
- C.K. Liu, Y.Z. Yang, S.Y. Guo, Y. Zeng, N. Zhu, X. Li, Z. Fang and K. Guo, Org. Biomol. Chem., 14, 8570 (2016); https://doi.org/10.1039/C6OB01387B
- X. Zhang, W. Yang and L. Wang, Org. Biomol. Chem., 11, 3649 (2013); https://doi.org/10.1039/c3ob40619a
- Y. Shao, Z. Wu, C. Miao and L.J. Liu, Organomet. Chem., 767, 60 (2014); https://doi.org/10.1016/j.jorganchem.2014.05.017
- B. Song, S. Wang, C. Sun, H. Deng and B. Xu, Tetrahedron Lett., 48, 8982 (2007); https://doi.org/10.1016/j.tetlet.2007.10.099
- H. Du, Q. Ruan, M. Qi and W. Han, J. Org. Chem., 80, 7816 (2015); https://doi.org/10.1021/acs.joc.5b01249
- M. Lamani and K.R. Prabhu, Chem. Eur. J., 18, 14638 (2012); https://doi.org/10.1002/chem.201202703
- X. Zhang and L. Wang, Green Chem., 14, 2141 (2012); https://doi.org/10.1039/c2gc35489f
- D. Wang, K. Zhang, L. Jia, D. Zhang, Y. Zhang, Y. Cheng, C. Lin and B. Wang, Org. Biomol. Chem., 15, 3427 (2017); https://doi.org/10.1039/C7OB00270J
- N. Mupparapu, R.A. Vishwakarma and Q.N. Ahmed, Tetrahedron, 71, 3417 (2015); https://doi.org/10.1016/j.tet.2015.03.088
- S. Guo, Z. Fang, Z. Yang, C. Liu, Z. Dai, L. Zhao and K. Guo, RSC Adv., 6, 1503 (2016); https://doi.org/10.1039/C5RA24062J
- Z. Zhang, J. Su, Z. Zha and Z. Wang, Chem. Commun., 49, 8982 (2013); https://doi.org/10.1039/c3cc43685c
- A. Suda, K. Kawasaki, S. Komiyama, Y. Isshiki, D.-O. Yoon, S.J. Kim, Y.-J. Na, K. Hasegawa, T.A. Fukami, S. Sato, T. Miura, N. Ono, T. Yamazaki, R. Saitoh, N. Shimma, Y. Shiratori and T. Tsukuda, Bioorg. Med. Chem., 22, 892 (2014); https://doi.org/10.1016/j.bmc.2013.11.036
- N. Nishimura, A. Kato and I. Maeba, Carbohydr. Res., 331, 77 (2001); https://doi.org/10.1016/S0008-6215(01)00017-9
- B. Klenke, M. Stewart, M.P. Barrett, R. Brun and I.H. Gilbert, J. Med. Chem., 44, 3440 (2001); https://doi.org/10.1021/jm010854+
- S. Naik, M. Kumaravel, J.T. Mague and M.S. Balakrishna, Inorg. Chem., 53, 1370 (2014); https://doi.org/10.1021/ic402150k
- C.-Y. Xiao, Y.-M. Li, H.-J. Lun, C.-Y. Cui and Y.-Q. Xu, J. Solid State Chem., 208, 127 (2013); https://doi.org/10.1016/j.jssc.2013.10.004
- S. Kotha, D. Kashinath and S. Kumar, Tetrahedron Lett., 49, 5419 (2008); https://doi.org/10.1016/j.tetlet.2008.07.021
- C.-H. Lee and T. Yamamoto, Bull. Chem. Soc. Jpn., 75, 615 (2002); https://doi.org/10.1246/bcsj.75.615
- M. Hernandez-Juarez, M. Vaquero, E. Alvarez, V. Salazar and A. Suarez, Dalton Trans., 42, 351 (2013); https://doi.org/10.1039/C2DT31907A
- P.K. Santra and P. Sagar, J. Mol. Catal. Chem., 197, 37 (2003); https://doi.org/10.1016/S1381-1169(02)00600-3
- Y. Iino, T. Karakida, N. Sugamata, T. Andoh, H. Takei, M. Takahashi, S. Yaguchi, T. Matsuno, M. Takehara, M. Sakato, S. Kawashima and Y. Morishita, Anticancer Res., 18, 171 (1998).
- S. Sahoo, S.K. Veliyath and M.C.B. Kumar, Int. J. Res. Pharm. Sci., 3, 326 (2012).
- M.K. Kathiravan, A.B. Salake, A.S. Chothe, P.B. Dudhe, R.P. Watode, M.S. Mukta and S. Gadhwe, Bioorg. Med. Chem., 20, 5678 (2012); https://doi.org/10.1016/j.bmc.2012.04.045
- T. Plech, J.J. Luszczki, M. Wujec, J. Flieger and M. Pizoñ, Eur. J. Med. Chem., 60, 208 (2013); https://doi.org/10.1016/j.ejmech.2012.11.026
- A. Diaz-Ortiz, A. de la Hoz, A. Moreno, A. Sanchez-Migallon and G. Valiente, Green Chem., 4, 339 (2002); https://doi.org/10.1039/B202014A
- H. Tanaka, K. Shizu, H. Miyazaki and C. Adachi, Chem. Commun., 48, 11392 (2012); https://doi.org/10.1039/c2cc36237f
- S. Achelle, Y. Ramondenc, F. Marsais and N. Plé, Eur. J. Org. Chem., 3129 (2008); https://doi.org/10.1002/ejoc.200800139
- F. Xie, M.-M. Chen, X.-T. Wang, H.-F. Jiang and M. Zhang, Org. Biomol. Chem., 12, 2761 (2014); https://doi.org/10.1039/C3OB42589D
- S. Biswas and S. Batra, Eur. J. Org. Chem., 3492 (2012); https://doi.org/10.1002/ejoc.201200276
- H. Gold, Angew. Chem., 72, 956 (1960); https://doi.org/10.1002/ange.19600722406
- H. Bredereck, F. Effenberger and A. Hofmann, Chem. Ber., 96, 3265 (1963); https://doi.org/10.1002/cber.19630961223
- K.R. Huffman and F.C. Schaefer, J. Org. Chem., 28, 1812 (1963); https://doi.org/10.1021/jo01042a017
- P. Wessig and J. Schwarz, Monatsh. Chem., 126, 99 (1995); https://doi.org/10.1007/BF00811762
- X. Xu, M. Zhang, H. Jiang, J. Zheng and Y. Li, Org. Lett., 16, 3540 (2014); https://doi.org/10.1021/ol501493h
- X. Ren, G. Wang, X. Tang and W. Zhao, Youji Huaxue, 35, 1733 (2015); https://doi.org/10.6023/cjoc201502014
- B. Niu, S. Li, C. Cui, Y. Yan, L. Tang and J. Wang, Eur. J. Org. Chem., 2019, 7800 (2019); https://doi.org/10.1002/ejoc.201901538
References
H.B. Deng, J.K. Jung, T. Liu, K.W. Kuntz, M.L. Snapper and A.H. Hoveyda, J. Am. Chem. Soc., 125, 9032 (2003); https://doi.org/10.1021/ja030249r
G.G. Xu and F.A. Etzkorn, Org. Lett., 12, 696 (2010); https://doi.org/10.1021/ol9027013
Z. Li, A.C. Ortega-Vilain, G.S. Patil, D.L. Chu, J.E. Foreman, D.D. Eveleth and J.C. Powers, J. Med. Chem., 39, 4089 (1996); https://doi.org/10.1021/jm950541c
S. Chatterjee, D. Dunn, M. Tao, G. Wells, Z.-Q. Gu, R. Bihovsky, M.A. Ator, R. Siman and J.P. Mallamo, Bioorg. Med. Chem. Lett., 9, 2371 (1999); https://doi.org/10.1016/S0960-894X(99)00392-3
M.M. Sheha, N.M. Mahfouz, H.Y. Hassan, A.F. Youssef, T. Mimoto and Y. Kiso, Eur. J. Med. Chem., 35, 887 (2000); https://doi.org/10.1016/S0223-5234(00)00187-2
Y.H. Chen, Y.H. Zhang, H.J. Zhang, D.Z. Liu, M. Gu, J.Y. Li, F. Wu, X.Z. Zhu, J. Li and F.J. Nan, J. Med. Chem., 49, 1613 (2006); https://doi.org/10.1021/jm050896o
K. Ni, L.G. Meng, K. Wang and L. Wang, Org. Lett., 20, 2245 (2018); https://doi.org/10.1021/acs.orglett.8b00586
D. Kumar, S.R. Vemula and G.R. Cook, ACS Catal., 6, 4920 (2016); https://doi.org/10.1021/acscatal.6b01116
C. De Risi, G.P. Pollini and V. Zanirato, Chem. Rev., 116, 3241 (2016); https://doi.org/10.1021/acs.chemrev.5b00443
K.K.S. Sai, P.A. Esteves, E.T. da Penha and D.A. Klumpp, J. Org. Chem., 73, 6506 (2008); https://doi.org/10.1021/jo801208m
Z. Zhang, Q. Zhang, Z. Ni and Q. Liu, Chem. Commun., 46, 1269 (2010); https://doi.org/10.1039/b917856b
H. Tanaka, A. Kuroda, H. Marusawa, H. Hatanaka, T. Kino, T. Goto, M. Hashimoto and T. Taga, J. Am. Chem. Soc., 109, 5031 (1987); https://doi.org/10.1021/ja00250a050
N. Fusetani, S. Matsunaga, H. Matsumoto and Y. Takebayashi, J. Am. Chem. Soc., 112, 7053 (1990); https://doi.org/10.1021/ja00175a045
C. Dugave, Curr. Org. Chem., 6, 1397 (2002); https://doi.org/10.2174/1385272023373301
X.J. Wang and F.A. Etzkorn, Biopolymers, 84, 125 (2006); https://doi.org/10.1002/bip.20240
H.H. Wasserman and A.K. Petersen, J. Org. Chem., 62, 8972 (1997); https://doi.org/10.1021/jo9718253
T. Higuchi, S. Uzu and M. Hirobe, J. Am. Chem. Soc., 112, 7051 (1990); https://doi.org/10.1021/ja00175a044
C.K. Liu, Z. Fang, Z. Yang, Q.W. Li, S.Y. Guo and K. Guo, RSC Adv., 6, 25167 (2016); https://doi.org/10.1039/C5RA27653E
U. Sharma, R. Sharma, R. Kumar, I. Kumar and B. Singh, Synthesis, 47, 2347 (2015); https://doi.org/10.1055/s-0034-1380435
R. Deshidi, S. Devari and B.A. Shah, Eur. J. Org. Chem., 1428 (2015); https://doi.org/10.1002/ejoc.201403547
S. Dutta, S.S. Kotha and G. Sekar, RSC Adv., 5, 47265 (2015); https://doi.org/10.1039/C5RA05671C
S.S. Kotha, S. Chandrasekar, S. Sahu and G. Sekar, Eur. J. Org. Chem., 7451 (2014); https://doi.org/10.1002/ejoc.201402961
S.S. Kotha and G. Sekar, Tetrahedron Lett., 56, 6323 (2015); https://doi.org/10.1016/j.tetlet.2015.09.053.
F.T. Du and J.X. Ji, Chem. Sci., 3, 460 (2012); https://doi.org/10.1039/C1SC00312G
W. Wei, Y. Shao, H.Y. Hu, F. Zhang, C. Zhang, Y. Xu and X.B. Wan, J. Org. Chem., 77, 7157 (2012); https://doi.org/10.1021/jo301117b
F. Liu, K. Zhang, Y. Liu, S. Chen, Y. Chen, D. Zhang, C. Lin and B. Wang, RSC Adv., 7, 7158 (2017); https://doi.org/10.1039/C6RA26679G
B. Du, B. Jin and P. Sun, Org. Biomol. Chem., 12, 4586 (2014); https://doi.org/10.1039/C4OB00520A
M. Ramanathan, C. Kuo and K.S.T. Liu, Org. Biomol. Chem., 14, 11446 (2016); https://doi.org/10.1039/C6OB02361D
N. Mupparapu, S. Khan, S. Battula, M. Kushwaha, A.P. Gupta, Q.N. Ahmed and R.A. Vishwakarma, Org. Lett., 16, 1152 (2014); https://doi.org/10.1021/ol5000204
C. Zhang, X.L. Zong, L.R. Zhang and N. Jiao, Org. Lett., 14, 3280 (2012); https://doi.org/10.1021/ol301130u
C. Zhang and N. Jiao, J. Am. Chem. Soc., 132, 28 (2010); https://doi.org/10.1021/ja908911n
R. Deshidi, M. Kumar, S. Devari and B.A. Shah, Chem. Commun., 50, 9533 (2014); https://doi.org/10.1039/C4CC03783A
M. Kumar, S. Devari, A. Kumar, S. Sultan, Q.N. Ahmed, M. Rizvi and B.A. Shah, Asian J. Org. Chem., 4, 438 (2015); https://doi.org/10.1002/ajoc.201500022
C. Zhang, Z.J. Xu, L.R. Zhang and N. Jiao, Angew. Chem. Int. Ed., 50, 11088 (2011); https://doi.org/10.1002/anie.201105285
C.K. Liu, Y.Z. Yang, S.Y. Guo, Y. Zeng, N. Zhu, X. Li, Z. Fang and K. Guo, Org. Biomol. Chem., 14, 8570 (2016); https://doi.org/10.1039/C6OB01387B
X. Zhang, W. Yang and L. Wang, Org. Biomol. Chem., 11, 3649 (2013); https://doi.org/10.1039/c3ob40619a
Y. Shao, Z. Wu, C. Miao and L.J. Liu, Organomet. Chem., 767, 60 (2014); https://doi.org/10.1016/j.jorganchem.2014.05.017
B. Song, S. Wang, C. Sun, H. Deng and B. Xu, Tetrahedron Lett., 48, 8982 (2007); https://doi.org/10.1016/j.tetlet.2007.10.099
H. Du, Q. Ruan, M. Qi and W. Han, J. Org. Chem., 80, 7816 (2015); https://doi.org/10.1021/acs.joc.5b01249
M. Lamani and K.R. Prabhu, Chem. Eur. J., 18, 14638 (2012); https://doi.org/10.1002/chem.201202703
X. Zhang and L. Wang, Green Chem., 14, 2141 (2012); https://doi.org/10.1039/c2gc35489f
D. Wang, K. Zhang, L. Jia, D. Zhang, Y. Zhang, Y. Cheng, C. Lin and B. Wang, Org. Biomol. Chem., 15, 3427 (2017); https://doi.org/10.1039/C7OB00270J
N. Mupparapu, R.A. Vishwakarma and Q.N. Ahmed, Tetrahedron, 71, 3417 (2015); https://doi.org/10.1016/j.tet.2015.03.088
S. Guo, Z. Fang, Z. Yang, C. Liu, Z. Dai, L. Zhao and K. Guo, RSC Adv., 6, 1503 (2016); https://doi.org/10.1039/C5RA24062J
Z. Zhang, J. Su, Z. Zha and Z. Wang, Chem. Commun., 49, 8982 (2013); https://doi.org/10.1039/c3cc43685c
A. Suda, K. Kawasaki, S. Komiyama, Y. Isshiki, D.-O. Yoon, S.J. Kim, Y.-J. Na, K. Hasegawa, T.A. Fukami, S. Sato, T. Miura, N. Ono, T. Yamazaki, R. Saitoh, N. Shimma, Y. Shiratori and T. Tsukuda, Bioorg. Med. Chem., 22, 892 (2014); https://doi.org/10.1016/j.bmc.2013.11.036
N. Nishimura, A. Kato and I. Maeba, Carbohydr. Res., 331, 77 (2001); https://doi.org/10.1016/S0008-6215(01)00017-9
B. Klenke, M. Stewart, M.P. Barrett, R. Brun and I.H. Gilbert, J. Med. Chem., 44, 3440 (2001); https://doi.org/10.1021/jm010854+
S. Naik, M. Kumaravel, J.T. Mague and M.S. Balakrishna, Inorg. Chem., 53, 1370 (2014); https://doi.org/10.1021/ic402150k
C.-Y. Xiao, Y.-M. Li, H.-J. Lun, C.-Y. Cui and Y.-Q. Xu, J. Solid State Chem., 208, 127 (2013); https://doi.org/10.1016/j.jssc.2013.10.004
S. Kotha, D. Kashinath and S. Kumar, Tetrahedron Lett., 49, 5419 (2008); https://doi.org/10.1016/j.tetlet.2008.07.021
C.-H. Lee and T. Yamamoto, Bull. Chem. Soc. Jpn., 75, 615 (2002); https://doi.org/10.1246/bcsj.75.615
M. Hernandez-Juarez, M. Vaquero, E. Alvarez, V. Salazar and A. Suarez, Dalton Trans., 42, 351 (2013); https://doi.org/10.1039/C2DT31907A
P.K. Santra and P. Sagar, J. Mol. Catal. Chem., 197, 37 (2003); https://doi.org/10.1016/S1381-1169(02)00600-3
Y. Iino, T. Karakida, N. Sugamata, T. Andoh, H. Takei, M. Takahashi, S. Yaguchi, T. Matsuno, M. Takehara, M. Sakato, S. Kawashima and Y. Morishita, Anticancer Res., 18, 171 (1998).
S. Sahoo, S.K. Veliyath and M.C.B. Kumar, Int. J. Res. Pharm. Sci., 3, 326 (2012).
M.K. Kathiravan, A.B. Salake, A.S. Chothe, P.B. Dudhe, R.P. Watode, M.S. Mukta and S. Gadhwe, Bioorg. Med. Chem., 20, 5678 (2012); https://doi.org/10.1016/j.bmc.2012.04.045
T. Plech, J.J. Luszczki, M. Wujec, J. Flieger and M. Pizoñ, Eur. J. Med. Chem., 60, 208 (2013); https://doi.org/10.1016/j.ejmech.2012.11.026
A. Diaz-Ortiz, A. de la Hoz, A. Moreno, A. Sanchez-Migallon and G. Valiente, Green Chem., 4, 339 (2002); https://doi.org/10.1039/B202014A
H. Tanaka, K. Shizu, H. Miyazaki and C. Adachi, Chem. Commun., 48, 11392 (2012); https://doi.org/10.1039/c2cc36237f
S. Achelle, Y. Ramondenc, F. Marsais and N. Plé, Eur. J. Org. Chem., 3129 (2008); https://doi.org/10.1002/ejoc.200800139
F. Xie, M.-M. Chen, X.-T. Wang, H.-F. Jiang and M. Zhang, Org. Biomol. Chem., 12, 2761 (2014); https://doi.org/10.1039/C3OB42589D
S. Biswas and S. Batra, Eur. J. Org. Chem., 3492 (2012); https://doi.org/10.1002/ejoc.201200276
H. Gold, Angew. Chem., 72, 956 (1960); https://doi.org/10.1002/ange.19600722406
H. Bredereck, F. Effenberger and A. Hofmann, Chem. Ber., 96, 3265 (1963); https://doi.org/10.1002/cber.19630961223
K.R. Huffman and F.C. Schaefer, J. Org. Chem., 28, 1812 (1963); https://doi.org/10.1021/jo01042a017
P. Wessig and J. Schwarz, Monatsh. Chem., 126, 99 (1995); https://doi.org/10.1007/BF00811762
X. Xu, M. Zhang, H. Jiang, J. Zheng and Y. Li, Org. Lett., 16, 3540 (2014); https://doi.org/10.1021/ol501493h
X. Ren, G. Wang, X. Tang and W. Zhao, Youji Huaxue, 35, 1733 (2015); https://doi.org/10.6023/cjoc201502014
B. Niu, S. Li, C. Cui, Y. Yan, L. Tang and J. Wang, Eur. J. Org. Chem., 2019, 7800 (2019); https://doi.org/10.1002/ejoc.201901538