Citation: Bin Sun, Wen-Peng Mai, Liang-Ru Yang, Pu Mao, Jin-Wei Yuan, Yong-Mei Xiao. A novel and facile synthesis of 4-arylquinolin-2(1H)-ones under metal-free conditions[J]. Chinese Chemical Letters, ;2015, 26(8): 977-979. doi: 10.1016/j.cclet.2015.05.008 shu

A novel and facile synthesis of 4-arylquinolin-2(1H)-ones under metal-free conditions

1.
School of Chemistry and Chemical Engineering, Henan University of Technology, Henan 450001, China

Corresponding author: Wen-Peng Mai, Pu Mao,
Received Date: 4 March 2015
Available Online: 20 April 2015
Fund Project: and the Plan for Scientific Innovation Talent of Henan University of Technology (No. 171147) (No. 131P-CXTD605)

A novel and facile synthesis of 4-arylquinolin-2(1H)-ones without metal catalysis has been developed. This reaction involved cyclization/elimination steps and was performed under metal-free conditions using inexpensive reagents such as NaI, selectfluor and KOH.
- 4-Arylquinolin-2(1H)-one,
- Metal-free,
- Selectfluor,
- Synthesis
1. [1]
  [1] (a) B. Joseph, F. Darro, A. Behard, et al., 3-Aryl-2-quinolone derivatives: synthesis and characterization of in vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration, J. Med. Chem. 45 (2002) 2543-2555; (b) L. Huang, M. Hsieh, C. Teng, K. Lee, S. Kuo, Synthesis and antiplatelet activity of phenyl quinolones, Biorg. Med. Chem. 6 (1998) 1657-1662; (c) M. Patel, R.J. McHugh, B.C. Cordova, et al., Synthesis and evaluation of quinoxalinones as HIV-1 reverse transcriptase inhibitors, Bioorg. Med. Chem. Lett. 10 (2000) 1729-1731; (d) M. Suzuki, Y. Ohuchi, K.T. Asanuma, et al., Synthesis and evaluation of novel 2-oxo-1,2-dihydro-3-quinolinecarboxamide derivatives as serotonin 5-HT4 receptor agonists, Chem. Pharm. Bull. 48 (2000) 2003-2008.
2. [2]
  [2] P. Desos, J.M. Lepagnol, P. Morain, P. Lestage, A.A. Cordi, Structure-activity relationships in a series of 2(¹H)-quinolones bearing different acidic function in the 3-position: 6,7-dichloro-2(¹H)-oxoquinoline-3-phosphonic acid, a new potent and selective AMPA/kainate antagonist with neuroprotective properties, J. Med. Chem. 39 (1996) 197-206.
3. [3]
  [3] (a) T.N. Glasnov, W. Stadlbauer, C.O. Kappe, Microwave-assisted multistep synthesis of functionalized 4-arylquinolin-2(¹H)-ones using palladium-catalyzed cross-coupling chemistry, J. Org. Chem. 70 (2005) 3864-3870; (b) P. Hewawasam, W. Fan, J. Knipe, et al., The synthesis and structure-activity relationships of 4-aryl-3-aminoquinolin-2-ones: a new class of calcium-dependent, large conductance, potassium (maxi-K) channel openers targeted for poststroke neuroprotection, Bioorg. Med. Chem. Lett. 12 (2002) 1779-1783.
4. [4]
  [4] (a) M. Marull, O. Lefebvre, M. Schlosser, An improved access to 4-trifluoromethyl-2(¹H)-quinolinones: the "watering protocol", Eur. J. Org. Chem. 1 (2004) 54-63; (b) B. Palakshi Reddy, P. Iniyavan, S. Sarveswari, V. Vijayakumar, Nickel oxide nanoparticles catalyzed synthesis of poly-substituted quinolines via Friedlander hetero-annulation reaction, Chin. Chem. Lett. 25 (2014) 1595-1600.
5. [5]
  [5] D.V. Kadnikov, R.C. Larock, Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines, J. Org. Chem. 69 (2004) 6772-6780.
6. [6]
  [6] (a) D.J. Tang, B.X. Tang, J.H. Li, Selective synthesis of 3-aryl quinolin-2(¹H)-ones and 3-(1-arylmethylene)oxindoles involving a 2-fold arene C-H activation process, J. Org. Chem. 74 (2009) 6749-6755; (b) P. Xie, Z.Q. Wang, G.B. Deng, et al., Copper-catalyzed aerobic oxidative carbocyclization-ketonization cascade: selective synthesis of quinolinones, Adv. Synth. Catal. 355 (2013) 2257-2262.
7. [7]
  [7] G. Battistuzzi, R. Bernini, S. Cacchi, I. De Salve, G. Fabrizi, 4-Aryl-2-quinolones through a pseudo-domino Heck/Buchwald-Hartwig reaction in a molten tetrabutylammonium acetate/tetrabutylammonium bromide mixture, Adv. Synth. Catal. 349 (2007) 297-302.
8. [8]
  [8] T. Iwai, T. Fujihara, J. Terao, Y. Tsuji, Iridium-catalyzed annulation of N-arylcarbamoyl chlorides with internal alkynes, J. Am. Chem. Soc. 132 (2010) 9602-9603.
9. [9]
  [9] W.P. Mai, G.C. Sun, J.T. Wang, et al., Silver-catalyzed radical tandem cyclization: an approach to direct synthesis of 3-acyl-4-arylquinolin-2(¹H)-ones, J. Org. Chem. 79 (2014) 8094-8102.
10. [10]
  [10] L. Shi, D. Zhang, R. Lin, et al., The direct C-H halogenations of indoles, Tetrahedron Lett. 55 (2014) 2243-2245.
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沈阳化工大学材料科学与工程学院沈阳 110142