References and Notes
- 2
Wiesner J.
Ortmann R.
Jomaa H.
Schlitzer M.
Angew. Chem. Int. Ed.
2003,
43:
5274
- 3
Gilles MH.
Management of Severe Malaria: A Practical Handbook
2nd ed.:
World Health Organization;
Geneva:
2000.
-
4a
O’Neill PM.
Mukhtar A.
Stocks PA.
Randle LE.
Hindley S.
Ward SA.
Storr RC.
Bickley JF.
O’Neil IA.
Maggs JL.
Hughes RH.
Winstanley PA.
Bray PG.
Park BK.
J. Med. Chem.
2003,
46:
4933
-
4b
Ridley RG.
Hofheinz W.
Matile H.
Jaquet C.
Dorn A.
Masciadri R.
Jolidon S.
Richter WF.
Guenzi A.
Girometta MA.
Urwyler H.
Huber W.
Thaithong S.
Peters W.
Antimicrob. Agents Chemother.
1996,
40:
1846
-
4c
Stocks PA.
Raynes KJ.
Bray PG.
Park BK.
O’Neill PM.
Ward SA.
J. Med. Chem.
2002,
45:
4975
-
4d
Vlahov R.
Pavrushev S.
Vlahov J.
Pure Appl. Chem.
1990,
62:
1303
-
4e
Madrid PB.
Sherrill J.
Liou AP.
Weisman JL.
DeRisi JL.
Kipling Guy R.
Bioorg. Med. Chem. Lett.
2005,
15:
1015
-
5a
Fournet A.
Vagneur B.
Richomme P.
Bruneton J.
Can. J. Chem.
1989,
67:
2116
-
5b
Fournet A.
Hocquemiller R.
Roblot F.
Cavé A.
Richomme P.
Bruneton J.
J. Nat. Prod.
1993,
56:
1547
-
5c
Fournet A.
Barrios AA.
Muñoz V.
Hocquemiller R.
Cavé A.
Richomme P.
Bruneton J.
Antimicrob. Agents Chemother.
1993,
37:
859
- 6
Fakhfakh MA.
Fournet A.
Prina E.
Mouscadet J.-F.
Franck X.
Hocquemiller R.
Figadere B.
Bioorg. Med. Chem.
2003,
11:
5013
-
7a
Steel PJ.
Coord. Chem. Rev.
1990,
106:
227
-
7b
Ernst S.
Kaim W.
J. Am. Chem. Soc.
1986,
108:
3578
-
7c
Mamo A.
Nicolleti S.
Cam Tat N.
Molecules
2002,
7:
618
-
7d
Qaseer H.
Croat. Chim. Acta
2005,
78:
79
- 8
Balasubramanian M.
Keay JG. In
Comprehensive Hetrocyclic Chemistry II
Vol. 5:
Katrizky AR.
Rees CW.
Scriven EFV.
Pergamon Press;
Oxford:
1996.
Chap. 5.06.
p.245
- 9
Manske RHF.
Kukla M.
Org. React.
1953,
7:
59
- 10 For a review on recent progress in the synthesis of quinolines, see: Kouznetsov VV.
Mendez LY.
Mendelez Gomez CM.
Curr. Org. Chem.
2005,
9:
141
-
For recent quinoline syntheses, see e.g.:
-
11a
Cho CK.
Oh BH.
Shim SC.
J. Heterocycl. Chem.
1999,
36:
1175
-
11b
Cho CK.
Oh BH.
Shim SC.
Tetrahedron Lett.
1999,
40:
1499
-
11c
Cho CK.
Oh BH.
Shim SC.
Oh DH.
J. Heterocycl. Chem.
2000,
37:
1315
-
11d
Cho CK.
Oh BH.
Kim JS.
Kim T.-J.
Shim SC.
Chem. Commun.
2000,
1885
-
11e
Sangu K.
Fuchibe K.
Akiyama T.
Org. Lett.
2004,
6:
353
-
11f
Jacob J.
Jones WD.
J. Org. Chem.
2003,
68:
3563
-
11g
Akiyama T.
Nakashima S.
Yokota K.
Fuchibe K.
Chem. Lett.
2004,
33:
922
-
12a
Cho CS.
Lee NY.
Kim T.-J.
Shim SC.
J. Heterocycl. Chem.
2004,
41:
409
-
12b
Cho CS.
J. Organomet. Chem.
2005,
690:
4094
-
13a
Braun RU.
Ansorge M.
Müller TJJ.
Chem. Eur. J.
2006,
12:
9081
-
13b
Müller TJJ.
Ansorge M.
Aktah D.
Angew. Chem. Int. Ed.
2000,
39:
1253
-
14a
Liao W.-W.
Müller TJJ.
Synlett
2006,
3469
-
14b
Schramm née Dediu OG.
Müller TJJ.
Adv. Synth. Catal.
2006,
348:
2565
-
14c
Schramm née Dediu OG.
Müller TJJ.
Synlett
2006,
1841
-
15a
Müller TJJ.
Targets in Heterocyclic Systems
2006,
10:
54
-
15b
Müller TJJ.
Chim. Oggi/Chemistry Today
2007,
25(1):
70
-
15c
D’Souza DM.
Müller TJJ.
Chem. Soc. Rev.
2007,
36:
1095
1 New address: Lehrstuhl für Organische Chemie, Institut für Organische Chemie und Makromolekulare Chemie der Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225 Düsseldorf, Germany.
16
Typical Procedure (3g, Table 1, Entry 7)
A magnetically stirred solution of 1d (234 mg, 1.00 mmol), 2a (139 mg, 1.05 mmol), (PPh3)2PdCl2
(20 mg, 0.02 mmol), and CuI (2 mg, 0.01 mmol) in degassed DBU (2 mmol) and THF (1.5 mL) was stirred under nitrogen in a heavy-walled SmithCreator process vial in the microwave cavity at 150 °C for 30 min. After cooling to r.t. EtOAc (40 mL) and H2O (40 mL) were added and the aqueous layer was extracted with EtOAc. The combined organic phases were dried with MgSO4 and the solvents were removed in vacuo. The residue was chromatographed on silica gel (hexane-EtOAc, 5:1) and recrystallized from EtOH or pentane-CHCl3 (1:1) to give 174 mg (79%) of 3g as light yellow crystals, mp 142 °C. 1H NMR (300 MHz, CDCl3): δ = 2.54 (s, 3 H), 7.44-7.54 (m, 3 H), 7.91 (d, J = 1.5 Hz, 1 H), 7.94 (d, J = 8.3 Hz, 1 H), 8.13 (d, J = 8.3 Hz, 1 H), 8.28 (dd, J = 8.3, 1.5 Hz, 2 H), 8.96 (d, J = 2.1 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ = 18.6 (CH3), 119.6 (CH), 121.3 (Cq), 127.8 (CH), 128.8 (CH), 129.9 (CH), 131.5 (Cq), 135.2 (CH), 137.1 (CH), 138.7 (Cq), 154.8 (Cq), 155.8 (CH), 159.3 (Cq). MS: (EI, 70 eV): m/z (%) = 220.1 (100) [M+], 205.1 (10) [M+ - CH3], 77 (12) [C6H5
+]. IR (KBr): ν = 3027, 1604, 1581, 1546, 1503, 1481, 1458, 1434, 1321, 1278, 1140, 1025, 898, 814, 766, 739, 703, 678, 568 cm-1. Anal. Calcd for C15H12N2 (220.3): C, 81.79; H, 5.49; N, 12.72. Found: C, 81.71; H, 5.38; N, 12.79.
17 All compounds have been fully characterized by 1H, 13C and DEPT, COSY, NOESY, HETCOR and HMBC NMR experiments, IR, mass spectrometry, HRMS, and/or combustion analyses.
18 CCDC-669319 (3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033; or deposit@ccdc.cam.ac.uk].