Alkali Salt-Catalyzed Aza-Michael Addition of 1,2,4-Triazole to α,β-Unsaturated Ketones and Imides

doi:10.6023/cjoc201907050

Abstract

An alkali salt-catalyzed highly efficient aza-Michael addition of 1,2,4-triazole to α,β-unsaturated ketones and imides has been developed, giving the desired products in moderate to excellent yields. The salient features of this reaction involve readily available starting materials, good substrate scope, mild condition, high efficiency and ease of scale-up. The product can be transformed into corresponding γ-aminoalcohol.

Key words: synthetic methods, Michael addition, enones, α,β-unsaturated imides, nitrogen heterocycles, 1,2,4-triazole

Cite this article

Ma Ben, Wang Ganggang, Zhou Hongyan, Yang Jingya. Alkali Salt-Catalyzed Aza-Michael Addition of 1,2,4-Triazole to α,β-Unsaturated Ketones and Imides[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 115-124.

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References

[1] (a) Zheng, K.; Liu, X.; Feng, X. Chem. Rev. 2018, 118, 7586.
(b) Gmach, J.; Błażewska, K. M. Synthesis 2016, 48, 2681.
(c) Sánchez-Roselló, M.; Aceña, J. L.; Simón-Fuentes, A.; del Pozo, C. Chem. Soc. Rev. 2014, 43, 7430.
(d) Amara, Z.; Caron, J.; Joseph, D. Nat. Prod. Rep. 2013, 30, 1211.
(e) Wang, J.; Li, P.; Choy, P. Y.; Chan, A. S. C.; Kwong, F. Y. ChemCatChem 2012, 4, 917.
(f) Enders, D.; Wang, C.; Liebich, J. X. Chem. Eur. J. 2009, 15, 11058.
(g) Xu, L. W.; Xia, C. G. Eur. J. Org. Chem. 2005, 633.
[2] (a) Roy, T. K.; Parhi, B.; Ghorai, P. Angew. Chem., Int. Ed. 2018, 57, 9397.
(b) Barát, V.; Csókás, D.; Bates, R. W. J. Org. Chem. 2018, 83, 9088.
(c) Wu, L.; Jin, R.; Li, L.; Hu, X.; Cheng, T.; Liu, G. Org. Lett. 2017, 19, 3047.
(d) Yang, X.; Chen, Z.; Cai, Y.; Huang, Y. Y.; Shibata, N. Green Chem. 2014, 16, 4530.
(e) Amara, Z.; Caron, J.; Joseph, D. Nat. Prod. Rep. 2013, 30, 1211.
(f) Mikami, K.; Fustero, S.; Sánchez-Roselló, M.; Aceña, J. L.; Soloshonok, V.; Sorochinsky, A. Synthesis 2011, 3045.
(g) Weiner, B.; Szymański, W.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L. Chem. Soc. Rev. 2010, 39, 1656.
(h) Vinogradov, M. G.; Turovaa, O. V.; Zlotin, S. G. Org. Biomol. Chem. 2019, 17, 3670.
[3] (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
(b) Bartoli, G.; Bosco, M.; Marcantoni, E.; Petrini, M.; Sambri, L.; Torregiani, E. J. Org. Chem. 2001, 66, 9052.
(c) Reboule, I.; Gil, R.; Collin, J. Tetrahedron Lett. 2005, 46, 7761.
(d) Loh, T. P.; Wei, L. L. Synlett 1998, 975.
(e) Wabnitz, T. C.; Spencer, J. B. Tetrahedron Lett. 2002, 43, 3891.
(f) Azizi, N.; Saidi, M. R. Tetrahedron 2004, 60, 383.
(g) Stanley, L. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2009, 48, 7841.
(h) Sukhorukov, A. Y.; Sukhanova, A. A.; Zlotin, S. G. Tetrahedron 2016, 72, 6191.
[4] (a) Gandelman, M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 2393.
(b) Wang, J.; Li, H.; Zu, L.; Wang, W. Org. Lett. 2006, 8, 1391.
(c) Uria, U.; Vicario, J. L.; Badía, D.; Carrillo, L. Chem. Commun. 2007, 2509.
(d) Wang, J.; Zu, L.; Li, H.; Xie, H.; Wang, W. Synthesis 2007, 2576.
(e) Madhavan, N.; Takatani, T.; Sherrill, C. D.; Weck, M. Chem. Eur. J. 2009, 15, 1186.
(f) Luo, G. S.; Zhang, S. L.; Duan, W. H.; Wang, W. Synthesis 2009, 1564.
(g) Lv, J.; Wu, H.; Wang, Y. Eur. J. Org. Chem. 2010, 11, 2073.
(h) Zhou, Y.; Li, X.; Li, W.; Wu, C.; Liang, X.; Ye, J. Synlett 2010, 2357.
(i) Guo, H. M.; Yuan, T. F.; Niu, H. Y.; Liu, J. Y.; Mao, R. Z. D.; Li, Y.; Qu, G. R. Chem. Eur. J. 2011, 17, 4095.
(j) Lee, S. J.; Youn, S. H.; Cho, C. W. Org. Biomol. Chem. 2011, 9, 7734.
(k) Li, H.; Zhao, J.; Zeng, L.; Hu, W. J. Org. Chem. 2011, 76, 8064.
(l) Uria, U.; Reyes, E.; Vicario, J. L.; Badía, D.; Carrillo, L. Org. Lett. 2011, 13, 336.
(m) Wang, J.; Wang, W.; Liu, X.; Hou, Z.; Lin, L.; Feng, X. Eur. J. Org. Chem. 2011, 11, 2039.
(n) Wu, H.; Tian, Z.; Zhang, L.; Huang, Y.; Wang, Y. Adv. Synth. Catal. 2012, 354, 2977.
(o) Lee, S. J.; Ahn, J. G.; Cho, C. W. Tetrahedron:Asymmetry 2014, 25, 1383.
(p) Chen, S. W.; Zhang, G. C.; Lou, Q. X.; Cui, W.; Zhang, S. S.; Hu, W. H.; Zhao, J. L. ChemCatChem 2015, 7, 1935.
(q) Kim, S.; Kang, S.; Kim, G.; Lee, Y. J. Org. Chem. 2016, 81, 4048.
(r) Bhagat, U. K.; Peddinti, R. K. Synlett 2018, 29, 99.
(s) Chittimalla, S. K.; Nakka, S.; Koodalingam, M.; Bandi, C. Synlett 2018, 29, 57.
(t) Bhagat, U. K.; Peddinti, R. K. J. Org. Chem. 2018, 83, 793.
[5] (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
(b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
(c) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
(d) Towns, A. D. Dyes Pigm. 1999, 42, 3.
(e) Hughes, G.; Bryce, M. R. J. Mater. Chem. 2005, 15, 94.
(f) Holmes, G.; Rice, A.; Snyder, K. C. R. J. Mater. Sci. 2006, 41, 4105.
(g) Kusama, H.; Sugihara, H.; Sayama, K. J. Phys. Chem. C 2009, 113, 20764.
[6] Ghannoum, M. A.; Rice, L. B. Clin. Microbiol. Rev. 1999, 12, 50.
[7] (a) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117.
(b) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
(c) Jagerovic, N.; Hernandez-Folgado, L.; Alkorta, I.; Goya, P.; Navarro, M.; Serrano, A.; de Fonseca, F. R.; Dannert, M. T.; Alsasua, A.; Suardiaz, M.; Pascual, D.; Martín, M. I. J. Med. Chem. 2004, 47, 2939.
(d) Papadopoulou, M. V.; Trunz, B. B.; Bloomer, W. D.; McKenzie, C.; Wilkinson, S. R.; Prasittichai, C.; Brun, R.; Kaiser, M.; Torreele, E. J. Med. Chem. 2011, 54, 8214.
(e) Moulin, A.; Demange, L.; Ryan, J.; Mousseaux, D.; Sanchez, P.; Bergé, G.; Gagne, D.; Perrissoud, D.; Locatelli, V.; Torsello, A.; Galleyrand, J. C.; Fehrentz, J. A.; Martinez, J. J. Med. Chem. 2008, 51, 689.
(f) Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; de Arellano, M. C. R.; Fuentes, A. S. J. Org. Chem. 2002, 67, 4667.
[8] (a) Huntsman, E.; Balsells, J. Eur. J. Org. Chem. 2005, 3761.
(b) Larsen, S. D.; DiPaolo, B. A. Org. Lett. 2001, 3, 3341.
(c) Stocks, M. J.; Cheshire, D. R.; Reynold, R. Org. Lett. 2004, 6, 2969.
(d) Zhang, J. P.; Lin, Y. Y.; Huang, X. C.; Chen, X. M. J. Am. Chem. Soc. 2005, 127, 5495.
(e) Ueda, S.; Nagasawa, H. J. Am. Chem. Soc. 2009, 131, 15080.
(f) Guru, M. M.; Punniyamurthy, T. J. Org. Chem. 2012, 77, 5063.
(g) Tam, A.; Armstrong, I. S.; La Cruz, T. E. Org. Lett. 2013, 15, 3586.
(h) Xu, H.; Ma, S.; Xu, Y.; Bian, L.; Ding, T.; Fang, X.; Zhang, W.; Ren, Y. J. Org. Chem. 2012, 80, 1758.
(i) Huang, H.; Guo, W.; Wu, W.; Li, C.; Jiang, H. Org. Lett. 2015, 17, 2894.
(j) Song, L.; Tian, X.; Lv, Z.; Li, E.; Wu, J.; Liu, Y.; Yu, W.; Chang, J. J. Org. Chem. 2015, 80, 7219.
(k) Chen, Z.; Li, H.; Dong, W.; Miao, M.; Ren, H. Org. Lett. 2016, 18, 1334.
(l) Yu, W.; Huang, Y.; Li, J.; Tang, X.; Wu, W.; Jiang, H. J. Org. Chem. 2018, 83, 9334.
(m) Li, H.; Wu, X.; Hao, W.; Li, H.; Zhao, Y.; Wang, Y.; Lian, P.; Zheng, Y.; Bao, X.; Wan, X. Org. Lett. 2018, 20, 5224.
[9] Liu, B. K.; Wu, Q.; Qian, X. Q.; Lv, D. S.; Lin, X. F. Synthesis 2007, 2653.
[10] Uddin, M. I.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2008, 1402.
[11] Dinér, P.; Nielsen, M.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983.
[12] Zhou, Y. F.; Li, X.; Li, W. L.; Wu, C. L.; Liang, X. M.; Ye, J. X. Synlett 2008, 1402.
[13] (a) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442.
(b) Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928.
(c) Madhavan, N.; Weck, M. Adv. Synth. Catal. 2008, 350, 419.
(d) Mazet, C.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, 1762.
(e) Madhavan, N.; Sommer, W.; Weck, M. J. Mol. Catal. A:Chem. 2011, 334, 1.
[14] Yang, J.; Ma, B.; Zhou, H.; Zhan, B.; Li, Z. Chin. J. Org. Chem. 2015, 35, 121(in Chinese). (杨靖亚, 马奔, 周红艳, 占宝华, 李政, 有机化学, 2015, 35, 121.)
[15] Yang, J.; Bao, Y.; Zhou, H.; Li, T.; Li, N.; Li, Z. Synthesis 2016, 48, 1139.
[16] Zhou, H.; Xiang, X.; Ma, B.; Wang, G.; Zhang, Z.; Yang, J. Synthesis 2019, 51, 3142.

碱金属盐催化1,2,4-三唑与α,β-不饱和酮及二酰亚胺的氮杂Michael反应