D
Z. Chen et al.
Letter
Synlett
Supporting Information
(16) Chen, Z.; Bi, J.; Su, W. K. Chin. J. Chem. 2013, 31, 507.
(17) Chen, Z. Yang X., Su W. 2015, 56, 2476.
(18) Kudale, A. A.; Kendall, J.; Warford, C. C.; Wilkins, N. D.; Bodwell,
G. J. Tetrahedron Lett. 2007, 48, 5077.
Supporting information for this article is available online at
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(19) (a) Gao, Q.; Liu, S.; Wu, X.; Zhang, J.; Wu, A. J. Org. Chem. 2015,
80, 5984. (b) Pottie, I. R.; Nandaluru, P. R.; Benoit, W. L.; Miller,
D. O.; Dawe, L. N.; Bodwell, G. J. J. Org. Chem. 2011, 76, 9015.
(c) Dang, A. T.; Miller, D. O.; Dawe, L. N.; Bodwell, G. J. Org. Lett.
2008, 10, 233.
(20) Pyrido[2,3-c]coumarins 4; General Procedure
A dry 25 mL flask was charged with 3-aminocoumarin (1a; 1
mmol), aromatic aldehyde 2 (1 mmol), ketone 3 (1 mmol),
MsOH (1 mmol), and MeCN (5 mL). The mixture was stirred at
the reflux temperature for 2.5−8 h until the reaction was com-
plete (TLC) and then cooled to r.t. The crystalline solids were
collected and washed with a little cold MeCN to give the pure
product.
References and Notes
(1) (a) Murray, R. D. H. Nat. Prod. Rep. 1995, 12, 477. (b) Estévez-
Braun, A.; González, A. G. Nat. Prod. Rep. 1997, 14, 465.
(c) Vermeer, C.; Schurgers, L. J. Hematol. Oncol. Clin. North Am.
2000, 14, 339. (d) Holbrook, A. M.; Pereira, J. A.; Labiris, R.;
McDonald, H.; Douketis, J. D.; Crowther, M.; Wells, P. S. Arch.
Intern. Med. 2005, 165, 1095. (e) Isambert, N.; Lavilla, R. Chem.
Eur. J. 2008, 14, 8444. (f) Touré, B. B.; Hall, D. G. Chem. Rev. 2009,
109, 4439.
(2) (a) Badran, M. M.; Ismail, M. M.; El-Hakeem, A. Egypt. J. Pharm.
Sci. 1992, 33, 1081. (b) El-Farargy, A. F. Egypt. J. Pharm. Sci. 1991,
32, 625. (c) Nofal, Z. M.; El-Masry, H.; Fahmy, H. H.; Sarhan, I.
Egypt. J. Pharm. Sci. 1997, 38, 1. (d) Nofal, Z. M.; El-Zahar, M. I.;
Abd-El-Karim, S. S. Molecules 2000, 5, 99. (e) Vijaykumar, P. R.;
Reddy, R. V.; Rao, V. R. Indian J. Chem., Sect. B: Org. Chem. Incl.
Med. Chem. 2003, 42, 1738. (f) Venugopala, K. N.; Jayashree, B. S.
Indian J. Heterocycl. Chem. 2003, 12, 307. (g) Vaccaro, W.; Yang,
B. V.; Kim, S.-H.; Huynh, T.; Tortolani, D. R.; Leavitt, K.; Li, W.;
Doweyko, A. M.; Chen, X.-. T.; Doweyko, L. WO 2004009017,
2004.
(3) Kulkarni, Y. D.; Srivastava, D.; Bishnoi, A.; Dua, P. R. J. Indian
Chem. Soc. 1996, 73, 173.
(4) Marcu, M. G.; Schulte, T. W.; Neckers, L. J. Natl. Cancer Inst. 2000,
92, 242.
(5) Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Detsi, A.;
Koufaki, M.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J. Eur. J.
Med. Chem. 2009, 44, 3020.
(6) Kolotilo, N. V.; Sinitsa, A. A.; Rassukana, Yu. V.; Onys’ko, P. P. Zh.
Obshch. Khim. 2006, 76, 1260; Chem. Abstr. 2006, 146, 316980.
(7) (a) Rodighiero, G.; Antonello, C. Boll. Chim. Farm. 1958, 97, 592.
(b) Irgolic, K. J. In Houben–Weyl; Klamann, D., Ed.; Thieme:
Stuttgart, 1990, 4th ed., Vol. E12b, 150.
(8) (a) Hammond, P. R.; Atkins, R. L. J. Heterocycl. Chem. 1978, 12,
1061. (b) Atkins, R. L.; Bliss, D. E. J. Org. Chem. 1978, 43, 1975.
(c) Grandberg, I. I.; Denisov, L. K.; Popova, O. A. Khim. Geterot-
sikl. Soedin. 1987, 2, 147.
(9) Fujimoto, A.; Sakurai, A.; Iwase, E. Bull. Chem. Soc. Jpn. 1976, 49,
809.
(10) Khan, M. A.; Gremal, A. L. J. Heterocycl. Chem. 1977, 14, 1009.
(11) Pavé, G.; Chalard, P.; Viaud-Massuard, M.-C.; Troin, Y.;
Guillaumet, G. Synlett 2003, 987.
(12) Majumdar, K. C.; Chattopadhyay, B.; Taher, A. Synthesis 2007,
3647.
(13) (a) Kudale, A. A.; Kendall, J.; Miller, D. O.; Collins, J. L.; Bodwell,
G. J. J. Org. Chem. 2008, 73, 8437. (b) Kudale, A. A.; Miller, D. O.;
Dawe, L. N.; Bodwell, G. J. Org. Biomol. Chem. 2011, 9, 7196.
(c) Khan, A. T.; Das, D. K.; Islam, K.; Das, P. Tetrahedron Lett.
2012, 53, 6418. (d) Belala, M.; Das, D. K.; Khan, A. T. Synthesis
2015, 47, 1109.
(14) (a) Dömling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083.
(b) Sadjadi, S.; Heravi, M. M. Tetrahedron 2011, 67, 2707.
(c) Wan, J.-P.; Liu, Y.-Y. RSC Adv. 2012, 2, 9763. (d) Isambert, N.;
Lavilla, R. Chem. Eur. J. 2008, 14, 8444. (e) Touré, B. B.; Hall, D. G.
Chem. Rev. 2009, 109, 4439.
3-(3-Chlorophenyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-
5-one (4f)
Pale-yellow powder; yield: 329 mg (86%); mp 241–243 °C; 1H
NMR (400 MHz, CDCl3): δ = 8.16 (s, 1 H), 8.09–8.06 (m, 1 H),
7.90 (s, 1 H), 7.57–7.55 (m, 3 H), 7.45–7.38 (m, 4 H), 7.36–7.33
(m, 2 H), 7.04 (d, J = 8.0 Hz, 1 H), 6.89–6.85 (m, 1 H); 13C NMR
(100 MHz, CDCl3): δ = 158.9, 155.9, 151.0, 149.3, 139.6, 139.4,
138.9, 135.2, 130.8, 130.3, 129.8, 129.4, 128.9, 128.3, 127.9,
127.7, 127.5, 125.6, 123.9, 117.9, 117.2. HRMS-ESI: m/z [M + H]+
calcd for C24H15ClNO2: 384.0786; found: 384.0794.
3-(1-Naphthyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-5-one
(4l)
Pale-yellow powder; yield: 331 mg (83%); mp 237–239 °C. 1H
NMR (400 MHz, CDCl3): δ = 8.24–8.23 (m, 1 H), 7.94–7.91 (m, 2
H), 7.84 (s, 1 H), 7.78–7.77 (m, 1 H), 7.53–7.46 (m, 8 H), 7.39 (d,
J = 8.0 Hz, 2 H). 7.11 (d, J = 8.0 Hz, 1 H) 6.92 – 6.88 (m, 1 H),
13C NMR (100 MHz, CDCl3): δ = 159.4, 158.6, 150.8 , 148.2,
139.2, 139.1, 136.1, 133.7, 131.9, 130.8, 130.3, 129.7, 129.3,
128.9, 128.3, 128.2, 128.0, 127.6, 126.8, 125.9, 125.0, 124.9,
123.5, 117.6, 116.9. HRMS-ESI: m/z [M + H]+ calcd for C28H18
-
NO2: 400.1332; found: 400.1327.
3-Phenyl-1-(4-tolyl)-5H-chromeno[3,4-b]pyridin-5-one (4m)
Pale-yellow powder; yield: 283 mg (78%); mp 208–210 °C. 1H
NMR (400 MHz,CDCl3): δ = 8.18–8.15 (m, 2 H), 7.90 (s, 1 H),
7.49–7.41 (m, 3 H), 7.35–7.29 (m, 6 H), 7.11 (d, J = 8.0 Hz, 1 H)
6.90–6.86 (m, 1 H), 2.49 (s, 3 H). 13C NMR (100 MHz, CDCl3):
δ = 158.7, 157.1, 150.7, 148.8, 139.0, 138.9, 136.9, 136.6, 130.0,
129.9, 129.9, 128.6, 128.1, 127.9, 127.5, 127.4, 127.1, 123.4,
117.5, 117.1, 21.4. HRMS-ESI: m/z [M + H]+ calcd for C25H18NO2:
364.1332; found: 364.1316.
1-(4-Fluorophenyl)-3-phenyl-5H-chromeno[3,4-b]pyridin-5-
one (4p)
White powder; yield: 315 mg (86%); mp 278–280 °C. 1H NMR
(400 MHz, DMSO-d6): δ = 8.31–8.29 (m, 2 H), 8.22 (s, 1 H), 7.63–
7.59 (m, 2 H), 7.57–7.51 (m, 3 H), 7.46–7.40 (m, 4 H), 7.02–6.94
(m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 164.2, 161.8, 158.6,
157.4, 150.8, 147.6, 139.2, 136.9, 135.6, 130.4, 130.1, 130.0,
128.8, 128.0, 127.4, 127.3, 127.2, 123.6, 117.8, 116.9, 116.7,
116.5. HRMS-ESI: m/z [M + H]+ calcd for C24H15FNO2: 368.1081;
found: 368.1065.
8-Phenyl-9,10,11,12-tetrahydro-6H-chromeno[3,4-c]iso-
quinolin-6-one (4v)
Pale-yellow powder; yield: 277 mg (85%); mp 217–219 °C. 1H
NMR (400 MHz, CDCl3): δ = 8.25 (d, J = 8.4 Hz, 1 H), 7.52–7.32
(m, 8 H), 3.36 (s, 2 H), 2.85 (s, 2 H), 1.88 (s, 4 H). 13C NMR (100
(15) Chen, Z.; Zhu, Q.; Su, W. Tetrahedron Lett. 2011, 52, 2601.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, A–E