Synlett 2014; 25(12): 1781-1785
DOI: 10.1055/s-0034-1378265
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Multisubstituted Tetrahydroquinolines through Aza-Michael/ Michael Addition Catalyzed by Quaternary Ammonium Salt

Li Zhang
a  Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: lpsong@shu.edu.cn
b  Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Yajun Li
c  School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, Hubei 430074, P. R. of China
b  Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Yafen Yuan
b  Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Bin Zhang
b  Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Yuan Gao
b  Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Yongming Wu*
b  Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Fax: +86(21)54925192   Email: ymwu@mail.sioc.ac.cn
,
Liping Song*
a  Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China   Email: lpsong@shu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 27 February 2014

Accepted after revision: 07 May 2014

Publication Date:
05 June 2014 (online)


Abstract

Multisubstituted tetrahydroquinolines were obtained in excellent yield from an array of N-[2-(3-oxo-3-phenylprop-1-enyl)phenyl]benzamide derivatives in a reaction catalyzed by quaternary ammonium salt. This method provides an efficient approach to the synthesis of densely substituted tetrahydroquinoline derivatives.

Supporting Information

 
  • References and Notes

    • 1a Michael JP. Nat. Prod. Rep. 2003; 20: 476
    • 1b Michael JP. Nat. Prod. Rep. 2007; 24: 223
    • 1c Sridharan V, Suryavanshi PA, Menendez JC. Chem. Rev. 2011; 111: 7157
    • 1d Asolkar RN, Schroder D, Heckmann R, Lang S, Wagner-Dobler I, Laatsch H. J. Antibiot. 2004; 57: 17
    • 1e Schmeda-Hirschmann G, Hormazabal E, Astudillo L, Rodriguez J, Theoduloz C. World J. Microbiol. Biotechnol. 2005; 21: 27
    • 1f Lombardo LJ, Camuso A, Clark J, Fager K, Gullo-Brown J, Hunt JT, Inigo I, Kan D, Koplowitz B, Lee F, McGlinchey K, Qian L, Ricca C, Rovnyak G, Traeger S, Tokarski J, Williams DK, Wu LI, Zhao Y, Manne V, Bhide RS. Bioorg. Med. Chem. Lett. 2005; 15: 1895
    • 1g Eastman RT, White J, Hucke O, Yokoyama K, Verlinde CL. M. J, Hast MA, Beese LS, Gelb MH, Rathod PK, Voorhis WC. V. Mol. Biochem. Parasitol. 2007; 152: 66
    • 1h Bulbule VJ, Rivas K, Verlinde CL. M. J, Voorhis WC. V, Gelb MH. J. Med. Chem. 2008; 51: 384
    • 1i Pagliero RJ, Lusvarghi S, Pierini AB, Brun R, Mazzieri MR. Bioorg. Med. Chem. 2010; 18: 142
    • 2a Bell S, Woustenberg B, Kaiser S, Menges F, Netscher T, Pfaltz A. Science 2006; 311: 642
    • 2b Pullmann T, Engendahl B, Zhang Z, Holscher M, Zanotti-Gerosa A, Dyke A, Francio G, Leitner W. Chem. Eur. J. 2010; 16: 7517
  • 3 Barros-Filho BA, Nunes FM, De Oliveira MC. F, Mafezoli J, Andrade-Neto M, Silveira ER, Pirani JR. Biochem. Syst. Ecol. 2004; 32: 817
  • 4 Ramesh E, Manian RD. R. S, Raghunathan R, Sainath S, Raghunathan M. Bioorg. Med. Chem. 2009; 17: 660
  • 5 Hiessbcock R, Wolf C, Richter E, Hitzler M, Chiba P, Kratzel M, Ecker G. J. Med. Chem. 1999; 42: 1921
  • 6 Liu W.-B, He H, Dai L.-X, You S.-L. Synthesis 2009; 2076
    • 7a Hamada Y, Kunimune I, Hara O. Heterocycles 2002; 56: 97
    • 7b Hara O, Sugimoto K, Hamada Y. Tetrahedron 2004; 60: 9381
    • 7c Hashmi AS. K. Chem. Rev. 2007; 107: 3180
    • 7d Hara O, Koshizawa T, Makino M, Kunimune I, Namiki A, Hamada Y. Tetrahedron 2007; 63: 6170
    • 7e Li Z, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
    • 7f Kothandaraman P, Foo SJ, Chan PW. H. J. Org. Chem. 2009; 74: 5947
    • 7g Arcadi A. Chem. Rev. 2008; 108: 3266
  • 8 Yin Y, Zhao G. Heterocycles 2006; 68: 23
    • 9a Bunce RA, Herron DM, Ackerman ML. J. Org. Chem. 2000; 65: 2847
    • 9b Arya P, Durieux P, Chen ZX, Josep R, Leek DM. J. Comb. Chem. 2004; 6: 54
    • 9c Arya P, Couve-Bonnaire S, Durieux P, Laforce D, Kumar R, Leek DM. J. Comb. Chem. 2004; 6: 735
    • 9d Sharma U, Srivastava S, Prakesch M, Sharma M, Leek DM, Arya P. J. Comb. Chem. 2006; 8: 735
    • 9e Prakesch M, Sharma U, Sharma M, Khadem S, Leek DM, Arya P. J. Comb. Chem. 2006; 8: 715
    • 9f Bunce RA, Nammalwar B, Slaughter LM. J. Heterocycl. Chem. 2009; 46: 854
  • 10 Steinhagen H, Corey EJ. Angew. Chem. Int. Ed. 1999; 38: 1928
    • 11a Shakya N, Roy KK, Saxena AK. Bioorg. Med. Chem. 2009; 17: 830
    • 11b Pagliero RJ, Lusvarghi S, Pierini AB, Brun R, Mazzieri MR. Bioorg. Med. Chem. 2010; 18: 142
  • 12 Yang W, He HX, Gao Y, Du DM. Adv. Synth. Catal. 2013; 355: 3670
  • 13 Corey EJ, Zhang FY. Org. Lett. 2000; 26: 4257
    • 14a Rauniyar V, Lackner AD, Hamilton GL, Toste FD. Science 2011; 334: 1681
    • 14b Rauniyar V, Wang ZJ, Burks HE, Toste FD. J. Am. Chem. Soc. 2011; 133: 8486
  • 15 CCDC-988606 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via https://www.ccdc.cam.ac.uk/services/structure_deposit/.
  • 16 Phipps RJ, Hiramatsu K, Toste FD. J. Am. Chem. Soc. 2012; 134: 8376
  • 17 Synthesis of 6a; Typical Procedure: A mixture of 5a (32.7 mg, 0.01 mmol), K3PO4 (84.9 mg, 0.04 mmol), and BnEt3NCl (2.28 mg, 0.001 mmol) in toluene (4 mL) was stirred at room temperature for 6 h. Upon completion of reaction as indicated by TLC, the solvent was evaporated and the residue was purified by flash chromatography on silica gel to provide the desired product 6a. 1H NMR (400 MHz, CDCl3): δ = 10.47 (s, 1 H), 7.98 (dd, J = 11.9, 4.7 Hz, 4 H), 7.89 (d, J = 8.1 Hz, 1 H), 7.59 (t, J = 7.4 Hz, 1 H), 7.52–7.43 (m, 6 H), 67.43–7.37 (m, 1 H), 7.37–7.27 (m, 4 H), 7.27–7.12 (m, 6 H), 7.09 (d, J = 7.6 Hz, 1 H), 7.00 (dd, J = 11.1, 4.1 Hz, 1 H), 6.93 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 7.0 Hz, 1 H), 6.39 (d, J = 7.8 Hz, 1 H), 6.15 (d, J = 6.9 Hz, 1 H), 4.41 (dd, J = 11.4, 6.9 Hz, 1 H), 4.26 (t, J = 9.0 Hz, 1 H), 3.63 (dd, J = 18.1, 8.7 Hz, 1 H), 3.43 (dd, J = 18.1, 2.7 Hz, 1 H); 13C NMR (100 MHz, CDCl3): δ = 200.05, 197.45, 170.36, 165.29, 138.67, 136.52, 136.32, 136.27, 135.52, 134.70, 134.43, 133.88, 133.49, 132.59, 131.40, 130.83, 129.17, 128.77, 128.68, 128.50, 128.44, 128.06, 128.01, 127.44, 127.38, 126.96, 126.81, 126.49, 125.66, 125.21, 125.06, 58.14, 55.14, 37.67, 34.79; IR (KBr): 3269, 3059, 2904, 1673, 1597, 1449, 1361, 1226, 972, 755 cm–1; MS (ESI): m/z = 655 [M + H+]; HRMS (ESI): m/z [M + H+] calcd. for C44H35N2O4 +: 655.2586; found: 655.25913.