Synthesis of 3-Acyl and 2-Acyl Imidazo [1, 2-a]pyridines by I2-Mediated Diamination of α, β-Unsaturated Ketones with 2-Aminopyridines
- Corresponding author: Yu Wenquan, wenquan_yu@zzu.edu.cn Chang Junbiao, changjunbiao@zzu.edu.cn
Citation:
Yu Wenquan, Song Lina, Tian Xianhai, Zhao Ting, Wang Manman, Wu Jie, Qiao Yan, Chang Junbiao. Synthesis of 3-Acyl and 2-Acyl Imidazo [1, 2-a]pyridines by I2-Mediated Diamination of α, β-Unsaturated Ketones with 2-Aminopyridines[J]. Chinese Journal of Organic Chemistry,
;2018, 38(6): 1530-1537.
doi:
10.6023/cjoc201712045
(a) Zhu, Y. -P. ; Fei, Z. ; Liu, M. -C. ; Jia, F. -C. ; Wu, A. -X. Org. Lett. 2013, 15, 378.
(b) Zhu, Y. -P. ; Liu, M. -C. ; Cai, Q. ; Jia, F. -C. ; Wu, A. -X. Chem. -Eur. J. 2013, 19, 10132.
(c) Gao, Q. ; Liu, S. ; Wu, X. ; Zhang, J. ; Wu, A. Org. Lett. 2015, 17, 2960.
(a) Huo, C. ; Tang, J. ; Xie, H. ; Wang, Y. ; Dong, J. Org. Lett. 2016, 18, 1016.
(b) Roslan, I. I. ; Ng, K. -H. ; Chuah, G. -K. ; Jaenicke, S. Adv. Synth. Catal. 2016, 358, 364.
(c) Ma, L. ; Wang, X. ; Yu, W. ; Han, B. Chem. Commun. 2011, 47, 11333.
(d) Wang, X. ; Ma, L. ; Yu, W. Synthesis 2011, 2445.
(e) Cao, H. ; Liu, X. ; Liao, J. ; Huang, J. ; Qiu, H. ; Chen, Q. ; Chen, Y. J. Org. Chem. 2014, 79, 11209.
(f) Zhan, H. ; Zhao, L. ; Liao, J. ; Li, N. ; Chen, Q. ; Qiu, S. ; Cao, H. Adv. Synth. Catal. 2015, 357, 46
(a) Monir, K. ; Bagdi, A. K. ; Mishra, S. ; Majee, A. ; Hajra, A. Adv. Synth. Catal. 2014, 356, 1105.
(b) Mishra, S. ; Monir, K. ; Mitra, S. ; Hajra, A. Org. Lett. 2014, 16, 6084.
Zhu, Y.; Li, C.; Zhang, J.; She, M.; Sun, W.; Wan, K.; Wang, Q.; Yin, B.; Liu, P.; Li, J. Org. Lett. 2015, 17, 3872.
doi: 10.1021/acs.orglett.5b01854
(a) Nguyen, T. B. ; Corbin, M. ; Retailleau, P. ; Ermolenko, L. ; Al-Mourabit, A. Org. Lett. 2015, 17, 4956.
(b) Nguyen, T. B. ; Ermolenko, L. ; Retailleau, P. ; Al-Mourabit, A. Org. Lett. 2016, 18, 2177.
(a) Couty, F. ; Evano, G. In Comprehensive Heterocyclic Chemistry Ⅲ, Vol. 11, Eds. : Katritzky, A. R. ; Ramsden, C. A. ; Scriven, E. F. V. ; Taylor, R. J. K., Elsevier, Oxford, 2008, pp. 409~499.
(b) Bagdi, A. K. ; Santra, S. ; Monir, K. ; Hajra, A. Chem. Commun. 2015, 51, 1555.
(c) Dymińska, L. Bioorg. Med. Chem. 2015, 23, 6087.
(d) Enguehard-Gueiffier, C. ; Gueiffier, A. Mini-Rev. Med. Chem. 2007, 7, 888.
(a) Mizushige, K. ; Ueda, T. ; Yukiiri, K. ; Suzuki, H. Cardiovasc. Drug Rev. 2002, 20, 163.
(b) Igawa, H. ; Takahashi, M. ; Kakegawa, K. ; Kina, A. ; Ikoma, M. ; Aida, J. ; Yasuma, T. ; Kawata, Y. ; Ashina, S. ; Yamamoto, S. ; Kundu, M. ; Khamrai, U. ; Hirabayashi, H. ; Nakayama, M. ; Nagisa, Y. ; Kasai, S. ; Maekawa, T. J. Med. Chem. 2016, 59, 1116.
(c) Trabanco, A. A. ; Tresadern, G. ; Macdonald, G. J. ; Vega, J. A. ; Lucas, A. I. ; Matesanz, E. ; García, A. ; Linares, M. L. ; Diego, S. A. A. ; Alonso, J. M. ; Oehlrich, D. ; Ahnaou, A. ; Drinkenburg, W. ; Mackie, C. ; Andrés, J. I. ; Lavreysen, H. ; Cid, J. J. Med. Chem. 2012, 55, 2688.
(d) Gladysz, R. ; Adriaenssens, Y. ; Winter, H. D. ; Joossens, J. ; Lambeir, A. ; Augustyns, K. ; Veken, P. V. J. Med. Chem. 2015, 58, 9238.
(a) Song, G. ; Zhang, Y. ; Li, X. Organometallics 2008, 27, 1936.
(b) John, A. ; Shaikh, M. M. ; Ghosh, P. Dalton Trans. 2009, 10581.
(c) Ke, C. -H. ; Kuo, B. -C. ; Nandi, D. ; Lee, H. M. Organometallics 2013, 32, 4775.
(a) Stasyuk, A. J. ; Banasiewicz, M. ; Cyrański, M. K. ; Gryko, D. T. J. Org. Chem. 2012, 77, 5552.
(b) Mutai, T. ; Sawatani, H. ; Shida, T. ; Shono, H. ; Araki, K. J. Org. Chem. 2013, 78, 2482.
(c) Firmansyah, D. ; Ciuciu, A. I. ; Hugues, V. ; Blanchard-Desce, M. ; Flamigni, L. ; Gryko, D. T. Chem. -Asian J. 2013, 8, 1279.
(d) Furukawa, S. ; Shono, H. ; Mutai, T. ; Araki, K. ACS Appl. Mater. Interfaces 2014, 6, 16065.
(e) Nagarajan, N. ; Velmurugan, G. ; Prakash, A. ; Shakti, N. ; Katiyar, M. ; Venuvanalingam, P. ; Renganathan, R. Chem. -Asian J. 2014, 9, 294.
(f) Yao, C. ; Xue, Z. ; Lian, M. ; Xu, X. ; Zhao, J. ; Zhou, G. ; Wu, Y. ; Yu, D. ; Wong, W. -Y. J. Organomet. Chem. 2015, 784, 31.
(a) Kang, S. ; Kim, R. Y. ; Seo, M. J. ; Lee, S. ; Kim, Y. M. ; Seo, M. ; Seo, J. J. ; Ko, Y. ; Choi, I. ; Jang, J. ; Nam, J. ; Park, S. ; Kang, H. ; Kim, H. J. ; Kim, J. ; Ahn, S. ; Pethe, K. ; Nam, K. ; No, Z. ; Kim, J. J. Med. Chem. 2014, 57, 52935.
(b) Hirayama, T. ; Okaniwa, M. ; Banno, H. ; Kakei, H. ; Ohashi, A. ; Iwai, K. ; Ohori, M. ; Mori, K. ; Gotou, M. ; Kawamoto, T. ; Yokota, A. ; Ishikawa, T. J. Med. Chem. 2015, 58, 8036.
(c) Moraski, G. C. ; Miller, P. A. ; Bailey, M. A. ; Ollinger, J. ; Parish, T. ; Boshoff, H. I. ; Cho, S. ; Anderson, J. R. ; Mulugeta, S. ; Franzblau, S. G. ; Miller, M. J. ACS Infect. Dis. 2015, 1, 85.
(d) Li, R. ; Wang, H. ; Li, Y. ; Wang, Z. ; Wang, X. ; Wang, Y. ; Ge, Z. ; Li, R. Eur. J. Med. Chem. 2015, 93, 381.
(e) Jaramillo, C. ; de Diego, J. E. ; Hamdouchi, C. ; Collins, E. ; Keyser, H. ; Sánchez-Martínez, C. ; del Prado, M. ; Norman, B. ; Brooks, H. B. ; Watkins, S. A. ; Spencer, C. D. ; Dempsey, J. A. ; Anderson, B. D. ; Campbell, R. M. ; Leggett, T. ; Patel, B. ; Schultz, R. M. ; Espinosa, J. ; Vieth, M. ; Zhang, F. ; Timm, D. E. Bioorg. Med. Chem. Lett. 2004, 14, 6095.
(f) Sanfilippo, P. J. ; Urbanski, M. ; Press, J. B. ; Dubinsky, B. ; Moore, J. B. J. Med. Chem. 1988, 31, 2221.
(a) Starrett, J. E. Montzka, T. A. ; Crosswell, A. R. ; Cavanagh, R. L. J. Med. Chem. 1989, 32, 2204.
(b) Anderson, M. ; Beattie, J. F. ; Breault, G. A. ; Breed, J. ; Byth, K. F. ; Culshaw, J. D. ; Ellston, R. P. A. ; Green, S. ; Minshull, C. A. ; Norman, R. A. ; Pauptit, R. A. ; Stanway, J. ; Thomas, A. P. ; Jewsbury, P. J. Bioorg. Med. Chem. Lett. 2003, 13, 3021.
Podergajs, S.; Stanovnik, B.; Tišler, M. Synthesis 1984, 263.
For representative examples, see:(a) Wang, H.; Wang, Y.; Liang, D.; Liu, L.; Zhang, J.; Zhu, Q. Angew. Chem., Int. Ed. 2011, 50, 5678.
(b) Mohan, D. C.; Rao, S. N.; Adimurthy, S. J. Org. Chem. 2013, 78, 1266.
(c) Reddy, K. R.; Reddy, A. S.; Shankar, R.; Kant, R.; Das, P. Asian J. Org. Chem. 2015, 4, 573.
(d) Kaswan, P.; Pericherla, K.; Saini, H. K.; Kumar, A. RSC Adv. 2015, 5, 3670.
(e) Kaswan, P.; Pericherla, K.; Rajnikant; Kumar, A. Tetrahedron 2014, 70, 8539.
(f) Xing, M.-M.; Xin, M.; Shen, C.; Gao, J.-R.; Jia, J.-H.; Li, Y.-J. Tetrahedron 2016, 72, 4201.
(g) Meng, X.; Zhang, J.; Chen, B.; Jing, Z.; Zhao, P. Catal. Sci. Technol. 2016, 6, 890.
(h) Yan, R.-L.; Yan, H.; Ma, C.; Ren, Z.-Y.; Gao, X.-A.; Huang, G.-S.; Liang, Y.-M. J. Org. Chem. 2012, 77, 2024.
(a) Tian, X. ; Song, L. Wang, Manman. ; Lv, Z. ; Wu, J. ; Yu, W. ; Chang, J. Chem. -Eur. J. 2016, 22, 7617.
(b) Liu, J. ; Wei, W. ; Zhao, T. ; Liu, X. ; Wu, J. ; Yu, W. ; Chang, J. J. Org. Chem. 2016, 81, 9326.
Li, J. ; Zhu, Y. ; Li, C. ; Liu, P. ; Wang, Y. CN 105801575, 2016[Chem. Abstr. 2016, 165, 274501. ]
CCDC 1539194(3a) and 1539195(4s) contain the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre.
(a) King, L. C. J. Am. Chem. Soc. 1944, 66, 894.
(b) Pearson, R. G. J. Am. Chem. Soc. 1947, 69, 3100.
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