D
Synlett
T. Q. Hung et al.
Letter
Funding Information
(16) Rival, Y.; Grassy, G.; Michel, G. Chem. Pharm. Bull. 1992, 40,
1
170.
17) Al-Tel, T. H.; Al-Qawasmeh, R. A. Eur. J. Med. Chem. 2010, 45,
848.
This research is funded by the Vietnam National Foundation for Sci-
ence and Technology Development (NAFOSTED) under grant number
(
(
5
104.012015.81.()
18) Anaflous, A.; Benchat, N.; Mimouni, M.; Abouricha, S.; Ben-
Hadda, T.; El-Bali, B.; Hakkou, A.; Hacht, B. Lett. Drug Des. Discov.
2
004, 1, 224.
Acknowledgment
(
19) Almirante, L.; Polo, L.; Mugnaini, A.; Provinciali, E.; Rugarli, P.;
Biancotti, A.; Gamba, A.; Murmann, W. J. Med. Chem. 1965, 8,
Many thanks are due to Dr. Pham Chien Thang, Lecturer in VNU-Ha-
noi University of Science for his help in the X-ray single-crystal struc-
ture analysis of compound 9f.
305.
(
(
(
(
(
(
20) Ribeiro, I. G.; da Silva, K. C. M.; Parrini, S. C.; de Miranda, A. L. P.;
Fraga, C. A. M.; Barreiro, E. J. Eur. J. Med. Chem. 1998, 33, 225.
21) Firmansyah, D.; Ciuciu, A. I.; Hugues, V.; Blanchard-Desce, M.;
Flamigni, L.; Gryko, D. T. Chem. Asian J. 2013, 8, 1279.
22) Stasyuk, A. J.; Banasiewicz, M.; Ventura, B.; Cyrański, M. K.;
Gryko, D. T. New J. Chem. 2014, 38, 189.
23) Stasyuk, A. J.; Banasiewicz, M.; Cyrański, M. K.; Gryko, D. T.
J. Org. Chem. 2012, 77, 5552.
24) Bagdi, A. K.; Santra, S.; Monir, K.; Hajra, A. Chem. Commun. 2015,
Supporting Information
Supporting information for this article is available online at
https://doi.org/10.1055/s-0037-1611957.
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51, 1555.
References and Notes
25) Tyagi, V.; Khan, S.; Bajpai, V.; Gauniyal, H. M.; Kumar, B.;
(
(
(
(
(
(
1) Sabir, S.; Alhazza, M. I.; Ibrahim, A. A. Catal. Sustain. Energy
Chauhan, P. M. S. J. Org. Chem. 2012, 77, 1414.
(26) Kielesiński, Ł.; Tasior, M.; Gryko, D. T. Org. Chem. Front. 2015, 2,
21.
(27) Hung, T. Q.; Hancker, S.; Villinger, A.; Lochbrunner, S.; Dang, T.
T.; Friedrich, A.; Breitsprecher, W.; Langer, P. Org. Biomol. Chem.
2015, 13, 583.
(28) Hung, T. Q.; Dang, T. T.; Villinger, A.; Sung, T. V.; Langer, P. Org.
Biomol. Chem. 2012, 10, 9041.
(29) Banerji, B.; Chatterjee, S.; Chandrasekhar, K.; Ghosh, S.;
Mukherjee, K.; Mandal, C. J. Org. Chem. 2018, 83, 13011.
(30) Pericherla, K.; Jha, A.; Khungar, B.; Kumar, A. Org. Lett. 2013, 15,
4304.
(31) Typical Procedure: Preparation of 5-Phenyl-5H-pyr-
ido[2',1':2,3]imidazo[4,5-b]indole (9a)
2016, 2, 99.
2) Vardanyan, R.; Hruby, V. Synthesis of Best-Seller Drugs; Elsevier:
London, UK, 2016, 868.
3) Tabassum, K.; Ekta, P.; Kavitkumar, P. Mini-Rev. Org. Chem.
2018, 15, 459.
4) Sellamuthu, S.; Gutti, G.; Kumar, D.; Kumar Singh, S. Mini-Rev.
Org. Chem. 2018, 15, 498.
5) Carril, M.; SanMartin, R.; Domínguez, E.; Tellitu, I. Green Chem.
2007, 9, 219.
6) Butera, J. A.; Antane, S. A.; Hirth, B.; Lennox, J. R.; Sheldon, J. H.;
Norton, N. W.; Warga, D.; Argentieri, T. M. Bioorg. Med. Chem.
Lett. 2001, 11, 2093.
(7) Sui, Z.; Zhang, X.; Li, X. PCT Int. Appl. 2006116513, 2006.
8) Kim, Y.-C.; Park, C.-S.; Ha, T.-S. PCT Int. Appl. WO 2006096030A,
(
Aniline (40 mg, 0.426 mmol, 1.5 equiv) was added to a pressure
tube that was charged with 7 (100 mg, 284 μmol, 1 equiv),
2006.
(9) Gormemis, A. E.; Ha, T. S.; Im, I.; Jung, K.-Y.; Lee, J. Y.; Park, C.-S.;
Pd (dba) (13 mg, 14 μmol, 0.05 equiv), Xantphos (16 mg, 28
2 3
Kim, Y.-C. ChemBioChem 2005, 6, 1745.
10) Langer, S. Z.; Arbilla, S.; Benavides, J.; Scatton, B. Adv. Biochem.
μmol, 0.1 equiv), CuI (5 mg, 28 μmol, 0.1 equiv) and sodium
tert-butoxide (164 mg, 1.7 mmol, 6 equiv) under argon. The
tube was back-flushed with argon several times. Then, degassed
anhydrous toluene (5 mL) was added under argon. The reaction
mixture was heated at 110 °C for 12 h. After cooling, the reac-
tion mixture was diluted with dichloromethane (20 mL), and
(
Psychopharmacol. 1990, 46, 61.
(
(
11) Harrison, T. S.; Keating, G. M. CNS Drugs 2005, 19, 65.
12) Gueiffier, A.; Mavel, S.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.;
Andrei, G.; Chavignon, O.; Teulade, J.-C.; Witvrouw, M.;
Balzarini, J.; De Clercq, E.; Chapat, J.-P. J. Med. Chem. 1998, 41,
®
the resulting mixture was filtered through a pad of Celite ,
5
108.
which was washed with dichloromethane (3 x 40 mL). The fil-
trate was concentrated in vacuo. The crude product was puri-
fied by flash chromatography (silica gel; hexane/dichlorometh-
(
(
(
13) Elhakmaoui, A.; Gueiffier, A.; Milhavet, J.-C.; Blache, Y.; Chapat,
J.-P.; Chavignon, O.; Teulade, J.-C.; Snoeck, R.; Andrei, G.; De
Clercq, E. Bioorg. Med. Chem. Lett. 1994, 4, 1937.
14) Lacerda, R. B.; de Lima, C. K. F.; da Silva, L. L.; Romeiro, N. C.;
Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. Bioorg. Med. Chem.
ane/ ethyl acetate, 8:1:1) to yield 9a (50 mg, 62%) as a yellowish
1
solid. Mp 168–170 °C. H NMR (500 MHz, CDCl
): δ = 8.18–8.13
3
(m, 1 H), 7.77–7.70 (m, 2 H), 7.68–7.61 (m, 2 H), 7.58–7.55 (m, 1
H), 7.55–7.47 (m, 3 H), 7.33 (dd, J = 6.1, 3.1 Hz, 2 H), 7.11 (ddd,
J = 9.3, 6.7, 1.4 Hz, 1 H), 6.70 (td, J = 6.7, 1.2 Hz, 1 H). 13C NMR
2
009, 17, 74.
15) Márquez-Flores, Y. K.; Campos-Aldrete, M. E.; Salgado-Zamora,
H.; Correa-Basurto, J.; Meléndez-Camargo, M. E. Med. Chem. Res.
(126 MHz, CDCl ): δ = 144.62, 141.03, 135.68, 131.37, 129.02,
3
2012, 21, 3491.
128.38, 126.80, 125.53, 122.90, 121.40, 120.90, 120.13, 118.72,
+
117.89, 117.49, 109.90, 109.78. HRMS (ESI): m/z [M + H] calcd
for C19H13N : 284.1188; found: 284.1190.
3
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Georg Thieme Verlag Stuttgart · New York — Synlett 2019, 30, A–D