乙酸酐促进的[3+3]环化反应合成2-喹啉酮衍生物
收稿日期: 2020-07-30
修回日期: 2020-08-25
网络出版日期: 2020-09-22
基金资助
云南省科技厅项目(2017FD156); 云南省高校科技创新团队资助项目.
Synthesis of 2-Quinolinone Derivatives via [3+3] Cyclization Promoted by Acetic Anhydride
Received date: 2020-07-30
Revised date: 2020-08-25
Online published: 2020-09-22
Supported by
the Applied Basic Research Project of Yunnan(2017FD156); the Program for Innovative Research Team Technology) in University of Yunnan Province
赵瑜 , 陈卓 , 陈雪冰 . 乙酸酐促进的[3+3]环化反应合成2-喹啉酮衍生物[J]. 有机化学, 2021 , 41(2) : 731 -737 . DOI: 10.6023/cjoc202007070
2-Quinolinone unit is frequently found in both natural products and pharmaceuticals. Furthermore, they are important heterocycle building blocks. Herein, a novel approach to the synthesis of 2-quinolinone derivatives has been established from [3+3] cyclization of β-enaminones with malonic acid promoted by acetic anhydride with yields of 70%~87%. The reaction is particularly attractive due to following advantages: simple starting materials, operational simplicity, concise synthetic route, easy purification, highly modifiability of target molecules and so on.
| [1] | (a) Cho J-Y.; Bae, S.-H.; Kim, H.-K.; Lee, M.-Y.; Choi, Y.-S.; Jin, B.-R.; Lee, H.-J.; Jeong, H.-Y.; Lee, Y.-G.; Moon, J.-K. J. Agric. Food Chem. 2015, 63, 3587. |
| [1] | (b) He J.; Lion U.; Sattler S.; Gollmick F.A.; Grabley S.; Cai J.; Meiners M.; Schünke H.; Schaumann K.; Dechert U.; Krohn M. J. Nat. Prod. 2005, 68, 1397. |
| [1] | (c) Freeman G.A.; Andrews III C.W.; Hopkins A.L.; Lowell G.S.; Schaller L.T.; Cowan J.R.; Gonzales S.S.; Koszalka G.W.; Hazen R.J.; Boone L.R.; Ferris R.G.; Creech K.L.; Roberts G.B.; Short S.A.; Weaver K.; Reynolds D.J.; Milton J.; Ren J.; Stuart D.I.; Stammers D.K.; Chan J.H. J. Med. Chem. 2004, 47, 5923. |
| [1] | (d) Godard A.; Fourquez J.M.; Tamion R.; Marsais F.; Quéguiner G. Synlett 1994, 235. |
| [1] | (e) Goossen L.J.; Deng G.; Levy L.M. Science 2006, 313, 662. |
| [1] | (f) Nakatsu T.; Johns T.; Kubo I.; Milton K.; Sakai M.; Chatani K.; Saito K.; Yamagiwa Y.; Kamikawa K. J. Nat. Prod. 1990, 53, 1508. |
| [2] | (a) Arya K.; Agarwal M. Bioorg. Med. Chem. Lett. 2007, 17, 86. |
| [2] | (b) Chen Y.-F.; Lin Y.-C.; Huang P.-K.; Chan H.-C.; Kuo S.-C.; Lee K.-H.; Huang L.-J. Bioorg. Med. Chem. Lett. 2013, 21, 5064. |
| [3] | Tedesco D.; Shaw A.N.; Bambal R.; Chai D.; Concha N.O.; Darcy M.G.; Dhanak D.; Fitch D.M.; Gates A.; Gerhardt W.G.; Halegoua D.L.; Han C.; Hofmann G.A.; Johnston V.K.; Kaura A.C.; Liu N.; Keenan R.M.; Lin-Goerke J.; Sarisky R.T.; Wiggall K.J.; Zimmerman M.N.; Duffy K.J. J. Med. Chem. 2006, 49, 3, 971. |
| [4] | Han S.; Zhang F.-F.; Qian H.-Y.; Chen L.-L.; Pu J.-B.; Xie X.; Chen J.-Z. J. Med. Chem. 2015, 58, 5751. |
| [5] | (a) Mizutani N.; Aoki Y.; Nabe T.; Ishiwara M.; Yoshino S.; Takagaki H.; Kohno S. Eur. J. Pharmacol. 2009, 602, 138. |
| [5] | (b) Ishiwara M.; Aoki Y.; Takagaki H.; Ui, Michio.; Okajima F.J. Pharmacol. Exp. Ther. 2003, 307, 583. |
| [6] | (a) Kulagowski J.J.; Baker R.; Curtis N.R.; Mawer I.M.; Moseley A.M.; Ridgill M.P.; Rowley M.; Stansfield I.; Leeson P.D. J. Med. Chem. 1994, 37, 1402. |
| [6] | (b) Uchida S.; Hiraoka S.; Namiki N. Chem. Pharm. Bull. 2015, 63, 354. |
| [7] | (a) Zhou T.; Wang D.; Qian J.; Zhao W. Chin. J. Org. Chem. 2017, 37, 1548. (in Chinese) |
| [7] | 周婷, 王道林, 钱建华, 赵伟, 有机化学, 2017, 37, 1548.). |
| [7] | (b) Zhao Q.; Yao C.; Wang X. Chin. J. Org. Chem. 2016, 36, 1932. (in Chinese) |
| [7] | 赵群, 姚昌盛, 王香善, 有机化学, 2016, 36, 1932.). |
| [7] | (c) Glasnov T.N.; Stadlbauer W.; Kappe C.O. J. Org. Chem. 2005, 70, 3864. |
| [7] | (d) Klásek A.; K?emen F.; K?emenová H.; Ly?ka A.; Rouchal M. Tetrahedron 2017, 73, 1583. |
| [7] | (e) Chilin A.; Marzano C.; Baccichetti F.; Simonato M.; Guiotto A. Bioorg. Med. Chem. Lett. 2003, 11, 1311. |
| [8] | (a) Manikandan R.; Jeganmohan M. Org. Lett. 2014, 16, 3568. |
| [8] | (b) Zhang X.; Liu H.; Jia Y.-A. Chem. Commun. 2016, 52, 7665. |
| [8] | (c) Wu J.-L.; Xiang S.-H.; Zeng J.; Leow M.; Liu X.-W. Org. Lett. 2015, 17, 222. |
| [9] | Zhong S.-S.; Huang P.; Wang X.-Y.; Lin M.; Ge C.-H. Chin. J. Org. Chem. 2018, 38, 1199. (in Chinese) |
| [9] | 仲帅帅, 黄鹏, 王兴越, 林觅, 葛春华, 有机化学, 2018, 38, 1199.). |
| [10] | (a) Chen X.; Cui X.; Wu Y. Org. Lett. 2016, 18, 2411. |
| [10] | (b) Ikbal M.; Banerjee R.; Atta S.; Jana A.; Dhara D.; Anoop A.; Singh N. D. P.Chem. Eur. J. 2012, 18, 11968.. |
| [11] | Kulkarni B.A.; Ganesan A. Chem. Commun. 1998, 7, 785. |
| [12] | Park S.-J.; Lee J.-C.; Lee K.-I. Bull. Korean Chem. Soc. 2007, 28, 1203. |
| [13] | Fu L.-Q.; Cao X.-J.; Wan J.-P.; Liu Y.-Y. Chin. J. Chem. 2020, 38, 254. |
| [14] | (a) Xu H.; Zhou B.; Zhou P.; Zhou J.; Shen Y.-H.; Yu F.-C.; Li L.-L. Chem. Commun. 2016, 52, 8002. |
| [14] | (b) Jiang B.; Yi M.-S.; Shi F.; Tu S.-J.; Pindi S.; McDowell P.; Li G.-G. Chem. Commun. 2012, 48, 808. |
| [14] | (c) Hu J.-D.; Cao C.-P.; Lin W.; Hu M.-H.; Huang Z.-B.; Shi D.-Q. J. Org. Chem. 2014, 79, 793. |
| [14] | (d) Hao W.-J.; Wang J.-Q.; Xu X.-P.; Zhang S.-L.; Ji S.-J. J. Org. Chem. 2013, 78, 12362. |
| [14] | (e) Yu F.-C.; Zhou B.; Xu H.; Chang K.-J.; Shen Y.-H. Tetrahedron Lett. 2015, 56, 837. |
| [14] | (f) Miao H.-J.; Wang L.-L.; Han H.-B.; Zhao,. Y.-D.; Wang, L.-Q.; Bu, Z.-W.Chem. Sci. 2020, 11, 1418. |
| [14] | (g) Wang L.-L.; Han H.-B.; Cui Z.-H.; Zhao J.-W.; Bu Z.-W.; Wang Q.-L. Org. Lett. 2020, 22, 873. |
| [14] | (h) Usman M.; Hu X.-D.; Liu W.-B. Chin. J. Chem. 2020, 38, 737. |
| [14] | (i) Cao W.-B.; Liu B.-B.; Xu X.-P.; Ji S.-J. Org. Chem. Front. 2018, 5, 1194. |
| [15] | (a) Makawana J.A.; Patel M.P.; Patel R.G.; Chin. Chem. Lett. 2012, 23, 427. |
| [15] | (b) Hundsd?rfer C.; Hemmerling H.J.; G?tz C.; Totzke F.; Bednarski P.; Borgne M.L.; Jose J. Bioorg. Med. Chem. 2012, 20, 2282. |
| [16] | Chen X.-B.; Bai H.-R.; Huang C. Chin. J. Org. Chem. 2017, 37, 881. (in Chinese) |
| [16] | 陈雪冰, 白海瑞, 黄超, 有机化学, 2017, 37, 881.). |
| [17] | Luo Q.; Huang R.; Xiao Q.; Yao Y.; Lin J.; Yan S.-J. J. Org. Chem. 2019, 84, 1999. |
/
| 〈 |
|
〉 |
