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4. (a) Friedländer, P. Ber. Dtsch. Chem. Ges. 1882, 15, 2572–2575; (b) Elderfield, R.
C. In Heterocyclic Compounds; Elderfield, R. C., Ed.; Wiley: New York, 1952; Vol.
4, pp 45–57; (c) Ubeda, J. I.; Villacampa, M.; Avendano, C. Synthesis 1998, 1176–
1180.
5. Wu, J.; Xia, H. G.; Gao, K. Org. Biomol. Chem. 2006, 4, 126–129.
6. (a) Strekowski, L.; Czamy, A. J. Fluoresc. Chem. 2000, 104, 281–284; (b) Hu, Y. Z.;
Zang, G.; Thummel, R. P. Org. Lett. 2003, 5, 2251–2253; (c) Arcadi, A.; Chiarini,
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7. Zolfigol, M. A.; Salehi, P.; Shiri, M.; Faal Rastegar, T.; Ghaderi, A. J. Iran. Chem.
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66 °C); Anal. Calcd for C13H13N: C, 85.21; H, 7.15; N, 7.64. Found: C, 85.13;
H, 7.25; N, 7.62. Analytical data were in full agreement with those already
reported in the literature for the same compound.19
9-Methyl-3,4-dihydroacridin-1(2H)-one (9): White solid (mp: 78–79 °C); Anal.
Calcd for C14H13NO: C, 79.59; H, 6.20; N, 6.63; O, 7.57. Found: C, 79.34; H, 6.19;
N, 6.78. Analytical data were in full agreement with those already reported in
the literature for the same compound.21
3,3,9-Trimethyl-3,4-dihydroacridin-1(2H)-one (11): Pale yellow solid (mp: 105–
106 °C); Anal. Calcd For C16H17NO: C, 80.30; H, 7.16; N, 5.85; O, 6.69. Found: C,
80.45; H, 7.25; N, 5.91. Analytical data were in full agreement with those
already reported in the literature for the same compound.22
1-(2-Methyl-4-phenylquinolin-3-yl)ethanone (13): Yellow solid (mp: 114–
115 °C); Anal. Calcd for C18H1NO: C, 82.73; H, 5.79; N, 5.36; O, 6.12. Found:
C, 82.81; H, 5.54; N, 5.45. Analytical data were in full agreement with those
already reported in the literature for the same compound.23
Ethyl 2-methyl-4-phenylquinoline-3-carboxylate (14): Yellow solid (mp: 99–
100 °C); Anal. Calcd for C19H17NO2: C, 78.33; H, 5.88; N, 4.81; O, 10.98. Found:
C, 78.43; H, 5.44; N, 4.76. Analytical data were in full agreement with those
already reported in the literature for the same compound.23
8. Bose, D. S.; Kumar, R. K. Tetrahedron Lett. 2006, 47, 813–816.
9. Ryabukhin, S. V.; Volochnyuk, D. M.; Plaskon, A. S.; Naumchik, V. S.;
Tolomachev, A. A. Synthesis 2007, 1214–1224.
10. Ghassamipour, S.; Sardarian, A. R. Tetrahedron Lett. 2009, 50, 514–519.
11. Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Shakouri-Nikcheh, M. Tetrahedron
Lett. 2008, 49, 5366–5368.
12. For a recent review on the Friedländer annulation see Marco-Contelles, J.;
Pérez-Mayoral, E.; Samadi, A.; do Carmo Carreiras, M.; Soriano, E. Chem. Rev.
2009, 109, 2652–2671.
9-Phenyl-2,3-dihydro-1H-cyclopenta[b]quinoline (15): White solid (mp: 129–
130 °C); Anal. Calcd for C18H15N: C, 88.13l; H, 6.16; N, 5.71. Found: C, 88.42; H,
6.25; N, 5.33. Analytical data were in full agreement with those already
reported in the literature for the same compound.23
9-Phenyl-3,4-dihydroacridin-1(2H)-one (16): Pale yellow solid (mp: 155–
156 °C); Anal. Calcd forC19H15NO: C, 83.49; H, 5.53; N, 5.12; O, 5.85. Found:
C, 83.64; H, 5.11; N, 5.43. Analytical data were in full agreement with those
already reported in the literature for the same compound.24
13. (a) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Tetrahedron Lett. 2001,
42, 3193–3195; (b) Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.
Heterocycles 2001, 55, 1599–1604; (c) Curini, M.; Epifano, F.; Marcotullio, M. C.;
Rosati, O. Eur. J. Org. Chem. 2002, 1562–1565; (d) Curini, M.; Epifano, F.;
Maltese, F.; Rosati, O. Tetrahedron Lett. 2002, 43, 4895–4897; (e) Curini, M.;
Epifano, F.; Maltese, F.; Rosati, O. Synlett 2003, 552–554; (f) Curini, M.; Epifano,
F.; Maltese, F.; Marcotullio, M. C. Eur. J. Org. Chem. 2003, 1631–1634; (g) Curini,
M.; Epifano, F.; Montanari, F.; Rosati, O.; Taccone, S. Synlett 2004, 1832–1834.
14. (a) Curini, M.; Epifano, F.; Genovese, S.; Marcotullio, M. C.; Rosati, O. Org. Lett.
2005, 1331–1333; (b) Curini, M.; Epifano, F.; Genovese, S. Tetrahedron Lett.
2006, 47, 4697–4700; (c) Curini, M.; Epifano, F.; Genovese, S. Tetrahedron Lett.
2007, 48, 2717–2720; (d) Genovese, S.; Epifano, F.; Pelucchini, C.; Curini, M.
Eur. J. Org. Chem. 2009, 1132–1135; (e) Genovese, S.; Epifano, F.; Pelucchini, C.;
Procopio, A.; Curini, M. Tetrahedron Lett. 2010, 51, 5992–5995; (f) Epifano, F.;
Genovese, S.; Rosati, O.; Tagliapietra, S.; Pelucchini, C.; Curini, M. Tetrahedron
Lett. 2011, 52, 568–571.
15. Muchowski, J. M.; Maddox, M. L. Can. J. Chem. 2004, 82, 461–478.
16. Experimental. General procedure for quinoline synthesis using Yb(OTf)3 2-
Aminoaryl ketone (1.0 mmol), carbonyl compound (1.0 mmol) (dissolved in
CH2Cl2 (1 ml) when needed) and the resulting solution was added Yb(OTf)3
(5 mol %) and stirred at room temperature for the appropriate time (see Table
1). After completion of the reaction by monitoring by TLC, eluent CH2Cl2, few
drops of NaOH 1 N were added, the precipitate formed filtered under vacuum
and the filtrate solution washed with H2O and extracted twice with CH2Cl2
(5 mL). The combined organic layers were dried over anhydrous Na2SO4 and
the solvent evaporated to dryness. The syrup obtained was finally purified by
SiO2 gel column chromatography (eluent CH2Cl2/MeOH 99:1) affording pure
quinoline.
3,3-Dimethyl-9-phenyl-3,4-dihydroacridin-1(2H)-one (17): Pale yellow solid
(mp: 240–241 °C); Anal. Calcd for C21H19NO: C, 83.69; H, 6.35; N, 4.65; O,
5.31. Found: C, 83.71; H, 6.39; N, 4.61. Analytical data were in full agreement
with those already reported in the literature for the same compound.24
7,8-Dihydro-6H-cyclopenta[b]-1,8-naphthyridine (19): white solid (mp: 91–
93 °C).
1H NMR5; (200 MHz, CDCl3) d 2.75 (t, 3H), 3.01 (t, 3H), 3.23 (q, 2H), 7.81–
7.53(m,4H), 8.34–8.07 (m, 2H); 13C NMR (50 MHz, CDCl3) d 23.7, 26.1, 34.5,
119.2, 123.4, 127.3, 132.2, 132.5, 151.67, 152.6, 164.3; GC/MS: M+ 170 (99) 43,
68, 79, 91, 120, 130, 158. Anal. Calcd for C11H10NO: C, 77.62; H, 5.92; N, 16.46.
Found: C, 77.67; H, 5.34; N, 16.99.
The degree of purity of each product listed in the paper was analyzed by GC/MS
with
a Hewlett Packard 6890 gas chromatograph equipped with a
12.5 mm  0.25 mm MetSil column couplet to HP Chem Station Software.
The carrier gas was helium at a pressure of 3.5 kg/cm2, and the column
temperature was programmed from 50 to 270 °C at 10 °C/min. The
chromatogram was obtained by using a reporting integrator. Mass spectra
were obtained from
a GCMS system operating in the EI mode at 70 eV,
equipped with a 12.5 mm  0.25 mm MetSil column and an HP5973 Mass
Selective Detector, by using the same chromatographic conditions reported
above. The column was connected to the mass spectrometer insource through
an open-split interface heated at 250 °C.
17. Pitzer, K. S. Acc. Chem. Res. 1974, 12, 271–276.
18. León, R.; de los Ríos, C.; Marco-Contelles, J.; Huertas, O.; Barril, X.; Luque, F. J.;
López, M. G.; Villarroya, M. Bioorg. Med. Chem. 2008, 16, 7759–7769. and
references herein cited.
19. Enugala, R.; Nuvvula, S.; Kotra, V.; Varala, R.; Adapa, S. R. Heterocycles 2008, 75,
2523–2533.
1-(2,4-Dimethylquinolin-3-yl)ethanone (3): Yellow solid (mp: 240–241 °C);
Anal. Calcd for C13H13NO: C, 78.36; H, 6.58; N, 7.03; O, 8.03. Found: C, 78.70;
H, 6.09; N, 6.85. Analytical data were in full agreement with those already
reported in the literature for the same compound.19
Ethyl 2,4-dimethylquinoline-3-carboxylate (5): Yellow solid (mp: 271–272 °C);
Anal. Calcd for C14H15NO: C, 73.34; H, 6.59; N, 6.11; O, 13.96. Found: C, 73.65;
H, 6.23; N, 6.05.Analytical data were in full agreement with those already
reported in the literature for the same compound.20
20. Varala, R.; Enugala, R.; Adapa, S. R. Synthesis 2006, 3825–3830.
21. Na, J. E.; Lee, K. Y.; Park, D. Y.; Kim, J. N. Bull. Korean Chem. Soc. 2005, 26, 323–
355.
22. Selvam, N. P.; Saravanan, C.; Muralidharan, D.; Perumal, P. T. J. Heterocycl.
Chem. 2006, 43, 1379–1382.
23. Wang, H. M.; Hou, R. S.; Cheng, H. T.; Chen, L. C. Heterocycles 2009, 78, 487–493.
24. Ali Zolfigol, M. A.; Salehi, P.; Ghaderi, A.; Shiri, M.; Tanbakouchian, Z. J. Mol.
Catal. A: Chem. 2006, 259, 253–258.
9-Methyl-2,3-dihydro-1H-cyclopenta[b]quinoline (7): White solid (mp: 64–