Paper
Dalton Transactions
3-([1,1′-Biphenyl]-4-yl)-4H-quinolizin-4-one (4g). Yellow solid 9.90 (d, J = 8.6 Hz, 1H), 7.77 (d, J = 7.6 Hz, 2H), 7.64 (d, J =
(78%). m.p. 187–188 °C. ATR–FTIR ν (cm−1): 1647 (CvO), 1622 7.4 Hz, 1H), 7.58–7.29 (m, 6H), 7.25 (d, J = 9.1 Hz, 1H), 7.01
(CvC), 1071, 772, 690. 1H-NMR (300 MHz, CDCl3) δ (ppm): (d, J = 9.2 Hz, 1H), 6.53 (d, J = 7.4 Hz, 1H). 13C-NMR (75 MHz,
9.27 (d, J = 7.3 Hz, 1H), 7.96–7.91 (m, 3H), 7.69–7.63 (m, 4H), CDCl3) δ (ppm): 163.4, 141.3, 138.0, 136.2, 135.9, 129.5, 129.1,
7.47–742 (m, 3H), 7.36–7.28 (m, 2H), 7.02 (t, J = 6.5 Hz, 1H), 128.3, 128.2, 127.9, 127.7, 127.5, 126.5, 126.5, 123.9, 122.6,
6.75 (d, J = 8.0 Hz, 1H). 13C-NMR (75 MHz, CDCl3) δ (ppm): 105.8. MS (EI, 70 eV) m/z (%): 271 (86) [M]+•, 243 (100)
157.3, 142.0, 141.1, 139.8, 137.0, 136.7, 129.3, 129.2, 128.9, [M – CO]+, 121 (24) [C12H8O]+. HR-MS (FAB+) m/z for C19H13NO [M]+:
127.8, 127.3, 127.2, 127.1, 125.5, 119.6, 115.5, 103.5. MS (EI, 70 calculated 271.0997, found 271.0997.
eV) m/z (%): 297 (100) [M]+•, 269 (80) [M − CO]+. HR-MS (FAB+)
m/z for C21H15NO [M]+: calculated 297.1154, found 297.1146.
3-(Naphthalen-2-yl)-4H-quinolizin-4-one (4h). Yellow solid
Acknowledgements
(79%). m.p. 220–221 °C. ATR–FTIR ν (cm−1): 1653 (CvO), 1618
(CvC), 1484, 1288, 790, 745. 1H-NMR (300 MHz, CDCl3) The authors would like to acknowledge the technical assist-
δ (ppm): 9.23 (s, 1H), 8.30 (s, 1H), 7.99–7.67 (m, 5H), 7.41 ance provided by Martin Cruz Villafañe, Luis Velasco and
(s, 3H), 7.28 (s, 1H), 6.98 (s, 1H), 6.74 (s, 1H). 13C-NMR Javier Pérez. We would also like to thank the DGAPA IB200312-
(75 MHz, CDCl3) δ (ppm): 157.4, 142.1, 137.2, 135.4, 133.7, 2 and CONACYT 129855 projects and CONACYT for the Ph.D.
132.7, 129.4, 128.4, 127.8, 127.7, 127.7, 127.6, 127.0, 126.0, grant extended to A. R.-S (227146).
125.9, 125.5, 120.0, 115.6, 103.6. MS (EI, 70 eV) m/z (%):
271 (100) [M]+•, 243 (78) [M − CO]+. HR-MS (FAB+) m/z for
C19H13NO [M]+: calculated 271.0997, found 271.0997.
References
3-(1-Methyl-1H-pyrrol-2-yl)-4H-quinolizin-4-one (4i). Yellow
solid (79%). m.p. 129–130 °C. ATR–FTIR ν (cm−1): 1643 (CvO),
1 (a) J. J. Vaquero and J. Alvarez-Builla, Heterocycles Contain-
ing a Ring-Junction Nitrogen, in Modern Heterocyclic Chem-
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1
1622 (CvC), 1529, 1491, 1300, 1073, 696. H-NMR (300 MHz,
CDCl3) δ (ppm): 9.20 (d, J = 7.4 Hz, 1H), 7.74 (d, J = 7.9 Hz,
1H), 7.48 (d, J = 8.8 Hz, 1H), 7.38–7.29 (m, 1H), 7.01 (t, J =
6.9 Hz, 1H), 6.76 (s, 1H), 6.70 (d, J = 7.9 Hz, 1H), 6.27–6.14
(m, 2H), 3.65 (s, 3H). 13C-NMR (75 MHz, CDCl3) δ (ppm):
157.0, 142.1, 139.0, 131.0, 129.2, 127.5, 125.5, 123.5, 115.4,
113.9, 110.0, 107.8, 103.1, 35.3. MS (EI, 70 eV) m/z (%): 224
(100) [M]+•, 196 (13) [M − CO]+, 181 (18) [M − CH3CO]+. HR-MS
(FAB+) m/z for C14H12N2O [M]+: calculated 225.1028, found
225.1034.
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3-(Furan-2-yl)-4H-quinolizin-4-one (4j). Yellow solid (83%).
m.p. 115–117 °C. IR (KBr) ν (cm−1): 1660 (CvO), 1626 (CvC),
1
1476, 1313, 740. H-NMR (300 MHz, CDCl3) δ (ppm): 9.22 (d,
J = 6.9 Hz, 1H), 8.23 (d, J = 8.1 Hz, 1H), 7.48 (s, 2H), 7.42 (d, J =
9.9 Hz, 1H), 7.28 (m, 1H), 7.02 (m, 1H), 6.75 (d, J = 8.1 Hz, 1H),
6.56 (s, 1H). 13C-NMR (75 MHz, CDCl3) δ (ppm): 154.6, 150.6,
141.5, 140.8, 131.9, 128.8, 127.4, 125.6, 115.7, 112.3, 111.5,
109.7, 103.8. MS (EI, 70 eV) m/z (%): 211 (100) [M]+•, 183 (20)
[M − CO]+, 154 (88) [C11H8N]+. HR-MS (FAB+) m/z for
C13H10NO2 [M + H]+: calculated 212.0712, found 212.0705.
3-(Thiophen-2-yl)-4H-quinolizin-4-one (4k). Yellow solid
(76%). m.p. 108–110 °C. ATR–FTIR ν (cm−1): 1643 (CvO), 1619
(CvC), 1482, 1072, 786, 728. 1H-NMR (300 MHz, CDCl3)
δ (ppm): 9.24 (d, J = 6.7 Hz, 1H), 8.15 (d, J = 7.9 Hz, 1H), 7.67
(s, 1H), 7.45 (d, J = 8.3 Hz, 1H), 7.36 (s, 1H), 7.30 (m, 1H), 7.12
(s, 1H), 7.04 (m, 1H), 6.74 (d, J = 7.8 Hz, 1H). 13C-NMR
(75 MHz, CDCl3) δ (ppm): 155.4, 140.8, 139.2, 132.8, 129.0,
127.7, 126.6, 126.0, 125.5, 123.1, 116.0, 114.4, 103.9. MS (EI, 70
eV) m/z (%): 27 (100) [M]+•, 199 (74) [M − CO]+, 154 (20)
[C11H8N]+. HR-MS (FAB+) m/z for C13H10NOS [M + H]+: calcu-
lated 228.0483, found 22.0486.
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2-Phenyl-1H-pyrido[1,2-a]quinolin-1-one (4l). Yellow solid
(83%). m.p. 194–195 °C. IR (KBr) ν (cm−1): 1646 (CvO), 1618
(CvC), 1534, 833, 696. 1H-NMR (300 MHz, CDCl3) δ (ppm):
Dalton Trans.
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