Synlett 2023; 34(20): 2433-2438
DOI: 10.1055/a-2103-9629
cluster
Special Issue Dedicated to Prof. Hisashi Yamamoto

Synthesis of Furo- and Thienoquinolines by Using an Amine Oxidase-Inspired Catalyst

Pradip Ramdas Thorve
,
Biplab Maji  ∗
The authors thank SERB (CRG/2019/001232) and Indian Institute of Science Education and Research Kolkata (ARF) for financial support. P.R.T. thanks University Grants Commission for a fellowship.
› Weitere Informationen
    Lizenzen und Reprints Alle Artikel dieser Rubrik


Dedicated to Professor Dr. Hisashi Yamamoto on the occasion of his 80th birthday

Abstract

We report the regioselective synthesis of furo- and thienoquinolines by using an amine oxidase-inspired catalyst (1,10-phenanthroline-5,6-dione) and an abundant Lewis acid (FeCl3) as a co-catalyst. The aerobic amine dehydrogenation proceeds under mild conditions and produces the quinolines in high yields. Mechanistic studies helped to identify the possible reaction intermediates and the specific role of the catalyst in the multistep cascade.

Key words

biomimetic catalyst - iron catalysis - aerobic oxidation - dehydrogenation - quinolines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2103-9629.
  • Supporting Information


Publikationsverlauf

Eingereicht: 30. April 2023

Angenommen nach Revision: 31. Mai 2023

Accepted Manuscript online:
31. Mai 2023

Artikel online veröffentlicht:
19. Juli 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

    • 1a Anzini M, Cappelli A, Vomero S, Giorgi G, Langer T, Hamon M, Merahi N, Emerit BM, Cagnotto A, Skorupska M, Mennini T, Pinto JC. J. Med. Chem. 1995; 38: 2692
      CrossrefPubMed
    • 1b Cruickshank PA, Lee FT, Lupichuk A. J. Med. Chem. 1970; 13: 1110
      CrossrefPubMed
    • 2a Afzal O, Kumar S, Haider MR, Ali MR, Kumar R, Jaggi M, Bawa S. Eur. J. Med. Chem. 2015; 97: 871
      CrossrefPubMed
    • 2b Kokatla HP, Sil D, Malladi SS, Balakrishna R, Hermanson AR, Fox LM, Wang X, Dixit A, David SA. J. Med. Chem. 2013; 56: 6871
      CrossrefPubMed
    • 2c Rechfeld F, Gruber P, Kirchmair J, Boehler M, Hauser N, Hechenberger G, Garczarczyk D, Lapa GB, Preobrazhenskaya MN, Goekjian P, Langer T, Hofmann J. J. Med. Chem. 2014; 57: 3235
      CrossrefPubMed
    • 2d Volpi G. Asian J. Org. Chem 2022; 11: e202200171
      Crossref
  • 3 Movassaghi M, Hill MD. J. Am. Chem. Soc. 2006; 128: 4592
    CrossrefPubMed
  • 4 Movassaghi M, Hill MD. Org. Lett. 2008; 10: 3485
    CrossrefPubMed
  • 5 McBurney RT, Slawin AM. Z, Smart LA, Yu Y, Walton JC. Chem. Commun. 2011; 47: 7974
    CrossrefPubMed
  • 6 Bouma MJ, Masson G, Zhu J. Eur. J. Org. Chem. 2012; 475
    Crossref
    • 7a Akula M, Yogeeswari P, Sriram D, Jha M, Bhattacharya A. RSC Adv. 2016; 6: 46073
      Crossref
    • 7b Bao L, Liu J, Xu L, Hu Z, Xu X. Adv. Synth. Catal. 2018; 360: 1870
      Crossref
    • 7c Chen P, Nan J, Hu Y, Kang Y, Wang B, Ma Y, Szostak M. Chem. Sci. 2020; 12: 803
      CrossrefPubMed
    • 7d Chinthapally K, Massaro NP, Padgett HL, Sharma I. Chem. Commun. 2017; 53: 12205
      CrossrefPubMed
  • 8 Qi L.-J, Shi C.-Y, Chen P.-F, Li L, Fang G, Qian P.-C, Deng C, Zhou J.-M, Ye L.-W. ACS Catal. 2021; 11: 3679
    CrossrefPubMed
    • 9a Anthony C. Biochem. J. 1996; 320: 697
      CrossrefPubMed
    • 9b Anthony C, Ghosh M. Curr. Sci. 1997; 72: 716
    • 9c Klinman JP, Bonnot F. Chem. Rev. 2014; 114: 4343
      CrossrefPubMed
    • 9d Largeron M. Org. Biomol. Chem. 2017; 15: 4722
      CrossrefPubMed
    • 9e Mure M. Acc. Chem. Res. 2004; 37: 131
      CrossrefPubMed
    • 9f Zhang R, Luo S. Chin. Chem. Lett. 2018; 29: 1193
      Crossref
    • 9g Zhang R, Zhang R, Luo S. Prog. Chem. (Beijing, China) 2020; 32: 1753
  • 10 Largeron MN, Neudorffe A, Fleury M.-B. Angew. Chem. Int. Ed. 2003; 42: 1026
    CrossrefPubMed
  • 11 Wendlandt AE, Stahl SS. Angew. Chem. Int. Ed. 2015; 54: 14638
    CrossrefPubMed
    • 12a Thorve PR, Maji B. Catal. Sci. Technol. 2021; 11: 1116
      Crossref
    • 12b Thorve PR, Maji B. Org. Lett. 2021; 23: 542
      CrossrefPubMed
    • 13a Thorve PR, Maji K, Maji B. Org. Chem. Front. 2023; 10: 480
      Crossref
    • 13b Wendlandt AE, Stahl SS. J. Am. Chem. Soc. 2014; 136: 506
      CrossrefPubMed
    • 13c Wendlandt AE, Stahl SS. J. Am. Chem. Soc. 2014; 136: 11910
      CrossrefPubMed
  • 14 Quinolines 3; General Procedure A 10 mL sealed tube was charged with the appropriate aniline derivative 1 (0.1 mmol), phd (0.020 mmol, 20 mol%), FeCl3 (0.010 mmol, 10 mol%), TsOH·H2O (0.010 mmol, 10 mol%), and PhNO2 (0.5 mL). Amine 2 (0.15 mmol) was added slowly, and the mixture was stirred at r.t. in the presence of O2 (balloon; 1 atm) for about 5 min. The tube was then capped and placed in a preheated oil bath at 80 °C for 36 h. When the reaction was complete, it was quenched with H2O (5 mL) and the mixture was extracted with EtOAc or CH2Cl2 (3 × 2 mL). The combined organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography [silica gel (100–200 or 200–400 mesh), EtOAc–hexane]. 4-(4-Methoxyphenyl)furo[2,3-c]quinoline (3aa) Colorless solid; yield: 22.0 mg (0.080 mmol, 80%); Rf = 0.4 (EtOAc–hexane, 2:98). 1H NMR (500 MHz, CDCl3): δ = 8.51 (d, J = 9.0 Hz, 2 H), 8.29 (d, J = 8.2 Hz, 1 H), 8.07 (d, J = 8.1 Hz, 1 H), 7.91 (d, J = 2.1 Hz, 1 H), 7.69 (t, J = 7.6 Hz, 1 H), 7.57 (t, J = 7.6 Hz, 1 H), 7.29 (d, J = 2.1 Hz, 1 H), 7.11 (d, J = 9.0 Hz, 2 H), 3.91 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 161.2, 147.4, 146.9, 144.4, 144.3, 130.8, 130.7, 129.9, 128.9, 127.7, 126.2, 123.3, 122.9, 114.2, 105.6, 55.5. HRMS (ESI+): m/z [M + H]+calcd for C18H14NO2: 276.1019; found: 276.1020. 4-(4-Methoxyphenyl)-8-methylthieno[2,3-c]quinoline (3da) Colorless solid; yield: 26.0 mg (0.085 mmol, 85%); Rf = 0.4 (EtOAc–hexane, 4:96). 1H NMR (500 MHz, CDCl3): δ = 8.17 (d, J = 8.4 Hz, 1 H), 8.11 (d, J = 8.9 Hz, 2 H), 8.01 (s, 1 H), 7.95 (d, J = 5.3 Hz, 1 H), 7.77 (d, J = 5.5 Hz, 1 H), 7.53 (d, J = 8.5 Hz, 1 H), 7.10 (d, J = 8.9 Hz, 2 H), 3.89 (s, 3 H), 2.59 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 160.8, 152.7, 143.6, 142.5, 136.3, 132.7, 132.0, 131.3, 130.2, 130.1, 129.6, 123.4, 122.5, 121.9, 114.2, 55.5, 21.9. HRMS (ESI+): m/z [M + H]+calcd for C19H16NOS: 306.0947; found: 306.0956. 4-(p-Tolyl)furo[2,3-c]quinoline (3ad) Colorless solid; yield: 20.0 mg (0.077 mmol, 77%); Rf = 0.5 (EtOAc–hexane, 5:95). 1H NMR (500 MHz, CDCl3): δ = 8.41 (d, J = 8.2 Hz, 2 H), 8.28 (d, J = 8.4 Hz, 1 H), 8.11 (d, J = 7.9 Hz, 1 H), 7.94 (d, J = 2.0 Hz, 1 H), 7.70 (t, J = 7.7 Hz, 1 H), 7.60 (t, J = 7.6 Hz, 1 H), 7.40 (d, J = 8.2 Hz, 2 H), 7.33 (d, J = 2.1 Hz, 1 H), 2.47 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 147.6, 146.9, 144.9, 144.5, 140.0, 133.7, 130.8, 130.3, 129.5, 129.1, 127.7, 126.4, 123.3, 123.2, 105.6, 21.6. HRMS (ESI+): m/z [M + H]+calcd for C18H14NO: 260.1070; found: 260.1057. 4-(2-Naphthyl)furo[2,3-c]quinoline (3al) Yellowish solid; yield: 19.0 mg (0.064 mmol, 64%); Rf = 0.5 (EtOAc–hexane, 2:98). 1H NMR (500 MHz, CDCl3): δ = 9.06 (d, J = 2.0 Hz, 1 H), 8.67 (d, J = 8.7 Hz, 1 H), 8.36 (d, J = 7.6 Hz, 1 H), 8.14 (d, J = 8.1 Hz, 1 H), 8.10–8.04 (m, 2 H), 8.00 (d, J = 2.0 Hz, 1 H), 7.97–7.91 (m, 1 H), 7.74 (t, J = 7.6 Hz, 1 H), 7.63 (t, J = 6.9 Hz, 1 H), 7.61–7.54 (m, 2 H), 7.36 (d, J = 2.1 Hz, 1 H). 13C NMR (126 MHz, CDCl3): δ = 147.7, 147.5, 144.5, 144.1, 134.3, 133.5, 133.3, 131.4, 130.0, 129.7, 129.3, 128.5, 128.1, 127.9, 127.2, 126.8, 126.5, 126.1, 123.4, 123.2, 105.8. HRMS (ESI+): m/z [M + H]+calcd for C21H14NO: 296.1070; found: 296.1065.
  • 15 CCDC 224516 contains the supplementary crystallographic data for compound 3fa. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
  • 16 Hanawa F, Fokialakis N, Skaltsounis A.-L. Planta Med. 2004; 70: 531
    Artikel in Thieme ConnectPubMed
    • 17a Liu Y, Liu M, Zhang D, Hua X, Wang B, Zhou S, Li Z. Chem. Res. Chin. Univ. 2016; 32: 952
      Crossref
    • 17b Roman G. Arch. Pharm. (Weinheim, Ger.) 2022; 355: 2100462
      CrossrefPubMed
    • 17c Ünver Y, Sancak K, Çelik F, Birinci E, Küçük M, Soylu S, Burnaz NA. Eur. J. Med. Chem. 2014; 84: 639
      CrossrefPubMed
  • 18 Jun JV, Chenoweth DM, Petersson EJ. Org. Biomol. Chem. 2020; 18: 5747
    CrossrefPubMed