Chinese Journal of Organic Chemistry >
Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates
Received date: 2020-08-12
Revised date: 2020-09-08
Online published: 2020-09-30
Supported by
the Fundamental Research Funds for the Central Universities, Southwest Minzu University(2018NQN35)
Using Morita-Baylis-Hillman (MBH) carbonates and active methylene compounds as raw materials, the key azide intermediates were obtained through two nucleophilic substitution reactions catalyzed by tertiary amine. Then, seventeen new multi-substituted 1,4-dihydroquinoline derivatives were obtained by sequential Staudinger/intramolecular aza-Wittig/isomeri- zation reactions of the azide intermediates with triphenylphosphine under mild conditions. The intermediates and target compounds are all new compounds, and their structures have been confirmed by IR, HRMS, 1H NMR and 13C NMR techniques.
Hongyan Shi , Ying Zhong , Zhigang Zhao . Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 677 -687 . DOI: 10.6023/cjoc202008020
| [1] | Liu Z.; Zhao R.; He N.; Li W. Chin. J. Org. Chem. 2018, 38, 1261. (in Chinese) |
| [1] | 刘子强, 赵冉, 贺妮, 李伟, 有机化学, 2018, 38, 1261.). |
| [2] | Yang M.; Hu X.; Ouyang B.; Xie W.; Liu J.-B. Tetrahedron 2019, 75, 3516. |
| [3] | Foley M.; Tilley L. Pharmacol. Ther. 1998, 79, 55. |
| [4] | Kaur K.; Jain M.; Reddy R.P.; Jain R. Eur. J. Med. Chem. 2010, 45, 3245. |
| [5] | Gorka A.P.; de Dios A.; Roepe P.D. J. Med. Chem. 2013, 56, 5231. |
| [6] | Vandekerckhove S.; D’hooghe M. Bioorg. Med. Chem. 2015, 23, 5098. |
| [7] | Shiomi S.; Misaka R.; Kaneko M.; Ishikawa H. Chem. Sci. 2019, 10, 9433. |
| [8] | Kartsev V.; Shikhaliev K.S.; Geronikaki A.; Medvedeva S.M.; Ledenyova I.V.; Krysin M.Y.; Petrou A.; Ciric A.; Glamoclija J.; Sokovic M. Eur. J. Med. Chem. 2019, 175, 201. |
| [9] | Peng X.-M.; Peng L.-P.; Li S.; Avula S.R.; Kannekanti V.K.; Zhang S.-L.; Tam K.Y.; Zhou C.-H. Future Med. Chem. 2016, 8, 1927. |
| [10] | Marvadi S.K.; Krishna V.S.; Sinegubova E.O.; Volobueva A.S.; Esaulkova Y.L.; Muryleva A.A.; Tentler D.G.; Sriram D.; Zarubaev V.V.; Kantevari S. Bioorg. Med. Chem. Lett. 2019, 29, 2664. |
| [11] | Matteelli A.; Carvalho A. C. C.; Dooley K.E.; Kritski A. Future Microbiol. 2010, 5, 849. |
| [12] | Plowright A.T.; Schaus S.E.; Myers A.G. Chem. Biol. 2002, 9, 607. |
| [13] | Ren Z.-L.; Lu W.-T.; Cai S.; Xiao M.-M.; Yuan Y.-F.; He P.; Ding M.-W. J. Org. Chem. 2019, 84, 14911. |
| [14] | Ma X.; Zhang X.; Xie G.; Awad J.M.; Zhang W. Tetrahedron Lett. 2019, 60, 151127. |
| [15] | Ma X.; Zhang X.; Awad J.M.; Xie G.; Qiu W.; Zhang W. Green Chem. 2019, 21, 4489. |
| [16] | Ivanov K.L.; Kravtsova A.A.; Kirillova E.A.; Melnikov M.Y.; Budynina E.M. Tetrahedron Lett. 2019, 60, 1952. |
| [17] | Tryniszewski M.; Bujok R.; Cmoch P.; Ganczarczyk R.; Kulszewicz-Bajer I.; Wrobel Z. J. Org. Chem. 2019, 84, 2277. |
| [18] | Wang H.-M.; Wang T.-S.; He S.-J.; Chen Z.-Y.; Hu Y.-G. J. Chem. Res. 2019, 43, 201. |
| [19] | Cai L.; Zhang K.; Chen S.; Lepage R.J.; Houk K.N.; Krenske E.H.; Kwon O. J. Am. Chem. Soc. 2019, 141, 9537. |
| [20] | Tukhtaev H.B.; Ivanov K.L.; Bezzubov S.I.; Cheshkov D.A.; Melnikov M.Y.; Budynina E.M. Org. Lett. 2019, 21, 1087. |
| [21] | Ciccolini C.; Mari G.; Favi G.; Mantellini F.; De Crescentini L.; Santeusanio S. Molecules 2019, 24, 3785. |
| [22] | Ma X.; Zhang X.; Awad J.M.; Xie G.; Qiu W.; Muriph R.E.; Zhang W. Tetrahedron Lett. 2020, 61, 151392. |
| [23] | Wu J.; Kong H.; Ding M. Chin. J. Org. Chem. 2016, 36, 1662. (in Chinese) |
| [23] | 武静, 孔晗晗, 丁明武, 有机化学, 2016, 36, 1662.). |
| [24] | Chen X.; Zhong Y.; Zhao Z.; Huang G. Synthesis 2017, 49, 5371. |
| [25] | Zhong Y.; Zhang H.; Ding M.-W. J. Heterocycl. Chem. 2015, 52, 330. |
| [26] | Zhong Y.; Wu L.; Ding M.-W. Synthesis 2012, 44, 3085. |
| [27] | Zhong Y.; Wang L.; Ding M.W. Tetrahedron 2011, 67, 3714. |
| [28] | Crystallographic data for 5i has been deposited with the Cambridge Crystallographic Data Centre as deposition number CCDC 2021914 . |
| [29] | Wei J.; Li Y.; Tao C.; Wang H.; Cheng B.; Zhai H.; Li Y. J. Org. Chem. 2018, 83, 835. |
| [30] | Han E.G.; Kim H.J.; Lee K.J. Tetrahedron 2009, 65, 9616. |
| [31] | Procopio A.; Cravotto G.; Oliverio M.; Costanzo P.; Nardi M.; Paonessa R. Green Chem. 2011, 13, 436. |
| [32] | Stokes B.J.; Liu S.; Driver T.G. J. Am. Chem. Soc. 2011, 133, 4702. |
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