Synlett 2014; 25(19): 2721-2726
DOI: 10.1055/s-0034-1379248
cluster
© Georg Thieme Verlag Stuttgart · New York

An Unprecedented Tandem Annulation of ω-Azido-1-alkynes with Diaryl­iodonium Salts: A Facile Synthesis of Polycyclic Quinolines

Junjie Chen
a  Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Email: chenchao01@mails.tsinghua.edu.cn
,
Chao Chen*
a  Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Email: chenchao01@mails.tsinghua.edu.cn
,
Jing Chen
a  Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Email: chenchao01@mails.tsinghua.edu.cn
b  School of Chemical Engineering, Tianjin University, Tianjin 300072, P. R. of China
,
Hongpeng Gao
a  Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, P. R. of China   Email: chenchao01@mails.tsinghua.edu.cn
,
Hongmei Qu
b  School of Chemical Engineering, Tianjin University, Tianjin 300072, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 14 August 2014

Accepted after revision: 15 September 2014

Publication Date:
17 October 2014 (online)

Abstract

Polysubstituted quinolines are synthesized through an unprecedented cascade annulation of ω-azido-1-alkynes with diaryliodonium salts, which serve as C2-building blocks. The reaction proceeds smoothly and is catalyzed by Cu(I) catalysts to give various quinolines in good isolated yields with simple operation under mild conditions.

Supporting Information

 
  • References and Notes

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  • 8 Preparation of 3aa; Typical Procedure: 6-Azido-1-phenyl-1-hexyne (2a; 0.3 mmol, 59.7 mg) was added to a solution of diphenyliodonium trifluoromethanesulfonate (1a; 0.6 mmol, 258 mg) and Cu2O (0.045 mmol, 6.5 mg) in anhydrous DCE (2.0 mL) under a N2 atmosphere. The reaction mixture was stirred at 60 °C for 24 h, and then poured into a mixture of sat. aq NaHCO3 (5 mL) and CH2Cl2 (20 mL). The organic phase was separated, washed with sat. aq NaHCO3 (2 × 5 mL), and then dried over anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided 9-phenyl-2,3-dihydro-1H-cyclopenta[b]quinoline (3aa; 55 mg, 75% isolated yield) as a yellow solid. This product has been reported previously.5 9-Phenyl-2,3-dihydro-1H-cyclopenta[b]quinoline (3aa): 1H NMR (400 MHz, CDCl3): δ = 8.07 (dd, J = 8.8, 1.0 Hz, 1 H), 7.66–7.58 (m, 2 H), 7.56–7.42 (m, 3 H), 7.42–7.32 (m, 3 H), 3.24 (t, J = 7.7 Hz, 2 H), 2.91 (t, J = 7.4 Hz, 2 H), 2.17 (quint, J = 7.5 Hz, 2 H). 13C NMR (101 MHz, CDCl3): δ = 167.68, 148.1, 142.8, 136.9, 133.8, 129.4 (2×CH), 129.0, 128.6 (2×CH), 128.4, 128.1, 126.3, 125.8, 125.6, 35.4, 30.5, 23.7. GC-MS: m/z calcd for C18H15N: 245; found: 245.
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  • 11 Preparation of 5aa; Typical Procedure: 7-Azido-1-phenyl-1-heptyne (4a; 0.3 mmol, 63.9 mg) was added to a solution of diphenyliodonium trifluoromethanesulfonate (1a; 0.6 mmol, 258 mg) and Cu2O (0.045 mmol, 6.5 mg) in anhydrous DCE (2.0 mL) under a N2 atmosphere. The reaction mixture was stirred at 60 °C for 24 h, and then poured into a mixture of sat. aq NaHCO3 (5 mL) and CH2Cl2 (20 mL). The organic phase was separated, washed with sat. aq NaHCO3 (2 × 5 mL), and then dried over anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided 9-phenyl-1,2,3,4-tetrahydroacridine (5aa; 52 mg, 67% isolated yield) as a yellow solid. This product has been reported5 previously. 9-Phenyl-1,2,3,4-tetrahydroacridine (5aa): 1H NMR (400 MHz, CDCl3): δ = 8.02 (d, J = 8.5 Hz, 1 H), 7.60 (ddd, J = 8.3, 5.1, 3.1 Hz, 1 H), 7.55–7.42 (m, 3 H), 7.35–7.27 (m, 2 H), 7.23 (dd, J = 8.0, 1.4 Hz, 2 H), 3.20 (t, J = 6.6 Hz, 2 H), 2.60 (t, J = 6.5 Hz, 2 H), 2.02–1.88 (m, 2 H), 1.84–1.70 (m, 2 H). 13C NMR (101 MHz, CDCl3): δ = 159.2, 146.6, 146.4, 137.3, 129.2 (2×CH), 128.7 (2×CH), 128.5, 128.5, 127.8, 126.8, 125.9, 125.5, 34.4, 28.2, 23.2, 23.1. GC-MS: m/z calcd for C19H17N: 259; found: 259.
  • 12 CCDC-1019165 (3da) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 13 Preparation of 7aa; Typical Procedure: 8-Azido-1-phenyl-1-octyne (6a; 0.3 mmol, 68.1 mg) was added to a solution of diphenyliodonium trifluoromethanesulfonate (1a; 0.6 mmol, 258 mg) and Cu2O (0.045 mmol, 6.5 mg) in anhydrous DCE (2.0 mL) under a N2 atmosphere. The reaction mixture was stirred at 60 °C for 24 h, and then poured into a mixture of sat. aq NaHCO3 (5 mL) and CH2Cl2 (20 mL). The organic phase was separated, washed with sat. aq NaHCO3 (2 × 5 mL), and then dried over anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided 11-phenyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline (7aa; 59 mg, 72% isolated yield) as a yellow solid. This product has been reported5 previously. 11-Phenyl-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline (7aa): 1H NMR (301 MHz, CDCl3): δ = 8.03 (d, J = 8.3 Hz, 1 H), 7.60 (ddd, J = 8.3, 6.5, 1.8 Hz, 1 H), 7.55–7.42 (m, 3 H), 7.36–7.27 (m, 2 H), 7.26–7.19 (m, 2 H), 3.32–3.23 (m, 2 H), 2.73–2.66 (m, 2 H), 1.91–1.77 (m, 4 H), 1.67–1.53 (m, 2 H). 13C NMR (76 MHz, CDCl3): δ = 165.0, 146.0, 145.6, 137.8, 134.0, 129.6 (2×CH), 128.8, 128.6 (2×CH), 128.3, 127.8, 127.1, 126.5, 125.7, 40.4, 32.1, 30.9, 28.7, 27.2. GC-MS: m/z calcd for C20H19N: 273; found: 273.

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