6
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26. General procedure for the Synthesis of 2-oxo-benzo[1, 4] oxazines
(24a-q, 25a-d and 26-29): To a solution of the compound 20a-f
(substituted 2-amino phenol; 0.2 mmol) in water was added 0.2 mmol
of compound 21a-i (substituted 2,4-dioxo-4-phynyl butanoic acid), or
22 or 23; and the reaction mixture was irradiated under ultrasonic
sonicator at 80 ˚C temperature for about 75-120 min. (depending upon
the substrate employed). The progress of reaction was monitored by
TLC. After completion of reaction, the reaction mixture was filtered
off, washed with distilled water (3 × 50 ml) and dried it, which
furnished the crude product. The crude product were purified either by
recrystallization using EtOAc/Hexane or EtOH; or by flash column
chromatography method over silica gel using 9:1 Hexane/ethyl acetate
as an eluent which afforded the pure desired 2-oxo-benzo[1,4]oxazines
24a-q, 25a-d and 26-29, respectively in excellent yield (76-98 %).
Characterization data of representative (Z)-7-nitro-3-(2-oxo-2-
phenylethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one (24n):
Yellowish solid; yield: 57.5 mg (89 %), m.p. 240-242 °C; FT-IR (KBr,
νmax/cm-1) 3436, 1763, 1622, 1596, 1268; 1H NMR (400 MHz) δ
8.06 - 8.00 (m, 4H), 7.83 – 7.81 (m, 1H), 7.62 (t, J = 7.3 Hz, 1H), 7.54
(t, J = 7.5 Hz, 2H), 6.99 (s, 1H); 13C NMR (100 MHz) 190.7, 156.1,
142.2, 141.1, 139.2, 138.3, 133.6, 131.3, 129.6, 128.0, 121.4, 117.4,
112.6, 96.0; HRMS (ESI) calcd. for C16H10N2O5 [M+H]+: 311.0590;
found 311.0595.
27. General procedure for the Synthesis of 2-oxo-quinoxaline
analogues (31a-b, 32a-b and 33a-b):To a solution of 0.2 mmol of
benzene-1,2-diamine 30a-b in water was added 0.2 mmol of
compound 21a or 22 or 23; and the reaction mixture was irradiated
under ultrasonic sonicator at 80 ˚C temperature for about 75-120 min.
(depending upon the substrate employed). Progress of reaction was
monitored by TLC. After completion of reaction, the reaction mixture
was filtered off, washed with distilled water (3 × 50 ml) and dried it,
which furnished the crude product. The crude product were purified
either by recrystallization using EtOAc/Hexane or EtOH; which
afforded the pure desired 2-oxo-quinoxaline analogues (31a-b, 32a-b
and 33a-b) having excellent yield (80-95 %).
20. (a) Stepanova, E. E.; Babenysheva, A. V.; Maslivets, A. N. Russ. J.
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Maslivets, A. N. Russ. J. Org. Chem. 2013, 49, 1762-1767; (c) Aliev,
Z. G.; Krasnykh, O. P.; Maslivets, A. N.; Atovmyan, L. O. Russ.
Chem. Bull. 2000, 49, 2045-2047;(d) Koini, E. N.; Papazafiri, P.;
Vassilopoulos, A.; Koufaki, M.; Horváth, Z.; Koncz, I.; Virág, L.;
Papp, G. J.; Varró, A.; Calogeropoulou, T. J. Med. Chem. 2009, 52,
2328-2340; (e) Ramesh, C.; Raju, B. R.; Kavala, V.; Kuo, C.-W.; Ya,
C.-Fa. Tetrahedron, 2011, 67, 1187-1192; (f) Jangili, P.; Kashanna, J.;
Das, B. Tetrahedron Letters, 2013, 54, 3453–3456; (g) Huo, C.; Dong,
J.; Su, Y.; Tang, J.; Chen, F. Chem. Commun. 2016, 52, 13341—
13344;(h) Feng, E.; Huang, H.; Zhou, Y.; Ye, D.; Jiang, H.; Liu, H. J.
Org. Chem. 2009, 74, 2846; (i) Feng, G.; Wu, J.; Dai, W.-M.
Tetrahedron Lett. 2007, 48, 401; (j) Yuan, Y.; Liu, G.; Li, L.;Wang,
Z.;Wang, L. J. Comb. Chem. 2007, 9, 158; (k) Xing, X.; Wu, J.; Feng,
G.; Dai, W.-M. Tetrahedron 2006, 62, 6774; (l) Kundu, N. G.;
Chaudhuri, G.; Upadhyay, A. J. Org. Chem. 2001, 66, 20; (m) Henry,
N.; Guillaumet, G.; Pujol, M. D. Tetrahedron Lett. 2004, 45, 1465.
21. For known compounds, see: (a) Xia, M. Faming Zhuanli Shenqing
Gongkai Shuomingshu, 2008, CN 101108860 A; (b) Mashevskaya, I.
V.; Tolmacheva, I. A.; Voronova, E. V.; Odegova, T. F.;
Aleksandrova, G. A.; Goleneva, A. F.; Kol'tsova, S. V.; Maslivets, A.
N. Pharm. Chem. J. (Translation of Khimiko-Farmatsevticheskii
Zhurnal), 2002, 36 (2), 33-35; (c) Iwanami, Y.; Seki, T.; Inagaki, T.
Bull. Chem. Soc. Jpn. 1971, 44 (5), 1316-1321; (d) Kozminykh, E. N.;
Igidov, N. M.; Shavkunova, G. A.; Kozminykh, V. O. Russ. Chem.
Bull. (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya),
1997, 46 (7), 1285-1290; (e) Gein, V. L.; Rassudikhina, N. A.;
Shepelina, N. V.; Vakhrin, M. I.; Babushkina, E. B.; Voronina, E. V.
Pharm. Chem. J. 2008, 42 (9), 529-532; (f) Xia, M.; Wu, B.; Xiang, G.
J. Fluor. Chem. 2008, 129 (5), 402-408; (g) Habash, M.; Taha, M. O.
Bioorg. Med. Chem. 2011, 19 (16), 4746-4771; (h) Reynisson, J.;
Court, W.; Neill, C. O.; Day, J.; Patterson, L.; McDonald, E.;
Workman, P.; Katan, M.; Eccles, S. A. Bioorg. Med. Chem. 2009, 17
(8), 3169-3176; (i) Maslivets, V. A.; Maslivets, A. N. Russ. J. Org.
Chem. 2012, 48 (9), 1233-1237 and references cited therein; (j) Lia,
X.; Liua, N.; Zhanga, H.; Knudsonb, S. E.; Slaydenb, R. A.; Tongea, P.
J. Bioorg. Med. Chem. Lett. 2010, 20 (21), 6306-6309; (k) Khalturina,
V. V.; Shklyaev, Yu. V.; Aliev, Z. G.; Maslivets, A. N. Russ. J. Org.
Chem. 2009, 45g(10), 1519-1522.
Characterization data of representative (Z)-3-(2-(anthracen-9-yl)-2-
oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one (32a):
Yellowish solid; yield: 64.6 mg (90 %), m.p. > 250 °C; FT-IR (Neat,
νmax/cm-1) 2920, 1671, 1596, 1455, 1131; 1H NMR (400 MHz) δ
11.86 (s, 1H), 8.66 (d, J = 6.0 Hz, 1H), 8.13 – 8.09 (m, 4H), 7.59 –
7.47 (m, 5H), 7.20 – 7.19 (m, 3H), 6.37 (d, J = 7.2 Hz, 1H); 13C NMR
(100 MHz) δ 193.7, 155.1, 144.5, 136.2, 130.5, 128.2, 127.9, 127.3,
126.8, 126.7, 125.9, 125.8, 125.0, 124.9, 124.7, 123.8, 116.3, 96.2;
HRMS (ESI) calcd. for C24H16N2O2 [M+H]+: 365.1212; found
365.1218.
22. For selected examples see: (a) Nicolaou, K. C.; Sugita, K.; Baran, P.
S.; Zhong, Y. L. Angew. Chem., Int. Ed. 2001, 40, 207; (b) Nicolaou,
K. C.; Baran, P. S.; Zhong, Y. L.; Sugita, J. Am. Chem. Soc. 2002,
124, 2212; (c) Largeron, M.; Neudörff er, A.; Vuilhorgne, M.; Blattes,
E.; Fleury, M.-B. Angew. Chem. Int. Ed. 2002, 41, 824; (d) Choudhary,
G.; Naganaboina, R. T.; Peddinti, R. K. RSC Adv. 2014, 4, 17969; (e)
Achari, B.; Mandal, S. B.; Dutta, P. K.; Chowdhury, C. Synlett 2004,
2449 and references therein; (f) Macias, F. A.; Marin, D.; Oliveros
Bastidas, A.; Molinillo, J. M. G. Nat. Prod. Rep. 2009, 26, 478; (g)
Ilas, J.; Stefanic Anderluh, P.; Sollner Dolenc, M.; Kikelj, D.
Tetrahedron 2005, 61, 7325 and references therein.
28. Synthesis of 3-(1H-indol-3-yl)-2H-benzo[b][1,4]oxazin-2-one (35):
To a solution of the compound 20a (130.8 mg, 1.20 mmol) in water
was added 3-Indoleglyoxylic acid 34 (226.9 mg, 1.20 mmol); and the
reaction mixture was irradiated under ultrasonic sonicator at 80 ˚C
temperature for about 180 min. The progress of reaction was monitored
by TLC. After completion of reaction, the reaction mixture was filtered
off, washed with distilled water (3 × 50 ml) and dried it, which
furnished the crude product. The crude product was further purified by
recrystalization using EtOAc/Hexane and EtOH; which afforded the
pure desired Cephalandole A 35 having good yield (255.4 mg, 81 %).
Yellowish solid; yield: 255 mg (81) %, m.p. 230-232 °C; FT-IR (KBr,
νmax/cm-1) 3292, 3053, 2921, 2852, 1713, 1604, 1428, 1151; 1H
NMR (400 MHz) δ 11.99 (s, 1H), 8.77 – 8.75 (m, 1H), 8.70 (s, 1H),
23. For selected recent examples, see: (a) Gabriele, B.; Salerno, G.; Veltri,
L.; Mancuso, R.; Li, Z.; Crispini, A.; Bellusci, A. J. Org. Chem. 2006,
71, 7895; (b) Bhadra, S.; Adak, L.; Samanta, S.; Maidul Islam, A. K.
M.; Mukherjee, M.; Ranu, B. C. J. Org. Chem. 2010, 75, 8533; (c)