3.
4.
Wang, S.; Miller, W.; Milton, J.; Vicker, N.; Stewart, A.; Charlton, P.;
Prakash, Mistry, icka, D.-H.; Denny, W. A. Bioorg. Med. Chem. Lett. 2002,
12, 415.
25.
Suh, M.-E.; Kang, M.-J.; Yoo, H.-W.; Park, S.-Y.; Lee, C.-O. Bioorg.
Med. Chem. 2000, 8, 2079.
26.
27.
Yoo, H.-W.; Suh, M.-E.; Park, S. W. J. Med. Chem. 1998, 41, 4716.
Kim, J. S.; Lee, H.-J.; Suh, M.-E.; Choo, H.-Y. P.; Lee, S. K.; Park, H. J.;
Kim, C.; Parkb, S. W.; Lee, C.-O. Bioorg. Med. Chem. 2004, 12, 3683.
Kuo, S.-C.; Ibuka, T.; Huang, L.-J.; Lien, J.-C.; Yean, S.-R.; Huang, S.-C.;
Lednicer, D.; Morris-Natschke, S.; Lee, K.-H. J. Med. Chem. 1996, 39,
1447.
Aly, A. A.; Ishak, E. A.; Alsharari, M. A.; Al-Muaikel, N. S.; Bedair, T. M.
I. J. Het Chem. 2012, 49, 9.
Aly, A. A.; Hassan, A. A.; Brown, A. B.; El-Shaieb, K. M.; Bedair, T. M. I.
J. Het. Chem., 2011, 48, 787.
Illescas, B.; Martin, N.; Segura, J. L.; Seoane, C.; Orti, E.; Viruela, P. M.;
Viruela, R. J. Org. Chem., 1995, 60, 5643-5650.
(a) Okafor, C. O. Tetrahedron, 1988, 44, 1187-1194. (b) Fries, K.; Ochwat,
P. Ber. Deut. Chem. Ges. 1923, 56B, 1291-1304; Chem Abstr. 1923, 17,
3334; (c) Agarwal, N. L. J. Chem. Eng. Data. 1975, 20, 199.
Vicker, N.; Burgess, L.; Chuckowree, I. S.; Dodd, R.; Folkes, A. J.;
Hardick, D. J.; Hancox, T. C.; Miller, W.; Milton, J.; Sohal, S.; Wang, S.;
Wren, S. P.; Charlton, P. A.; Dangerfield, W.; Liddle, C.; Mistry, P.;
Stewart, A. J.; Denny, W. A. J. Med. Chem. 2002, 45, 721.
Kaupp, G.; Naimi-Jamal, M. R. Eur. J. Org. Chem. 2002, 1368.
Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.;
Sharpless, K. B. Angew. Chem. Int. Ed. 2005, 44, 3275.
Blackmond, D. G.; Armstrong, A.; Coombe, V.; Wells, A. Angew. Chem.
Int. Ed. 2007, 46, 3798.
Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem. Int. Ed. 2006,
45, 8100.
Otto, S.; Engberts, J. B. F. N.; Kwak, J. C. T. J. Am. Chem. Soc. 1998, 120,
9517.
Bonar-Law, R. P. J. Org. Chem. 1996, 61, 3623.
Arenas, D. R. M.; Bonilla, C. A. M.; Kouznetsov, V. V. Org. Biomol.
Chem. 2013, 11, 3655.
(a) Tandon, V. K.; Maurya, H. K. Tetrahedron Lett. 2009, 50, 5896; (b)
Tandon, V. K.; Maurya, H. K. Tetrahedron Lett. 2010, 51, 3843.
Tandon , V. K.; Maurya, H. K.; Verma, M. K.; Kumar, R.; Shukla, P. K.
Eur. J. Med. Chem. 2010, 45, 2418.
Tandon, V. K.; Maurya, H. K.; Mishra, N. N.; Shukla, P. K. Bioorg Med
Chem Lett. 2011, 21, 6398.
Tandon, V. K.; Kumar, S.; Mishra, N. N.; Shukla, P. K. Eur. J. Med. Chem.
2012, 56, 375.
Shiri, M.; Zolfigol, M. A. Tetrahedron 2009, 65, 587.
Katritzky, A. R.; Fan, W.-Q.; Li, Q.-L.; Bayyuk, S. J. Het. Chem. 1989, 26,
885.
Agarwal, N. L.; Mittal, R. L., Phillipine Journal of Science 1978, 105, 125.
Ruzicka, E.; Bekarek, V.; Kandranal, J.; Collect. Czech. Chem. Commun.
1975, 40, 1738.
Koswatta, P. B.; Lovely, C. J. Nat. Prod. Rep. 2011, 28, 511.
Akee, R. K.; Carroll, T. R.; Yoshida, W. Y.; Scheuer, P. J.; Stout, T. J.;
Clardy, J. J. Org. Chem. 1990, 55, 1944.
28.
5.
6.
29.
30.
31.
32.
7.
8.
9.
10.
11.
33.
34.
Kaul B. L.; Piastra, B.; Wolf, V. Eur.Pat.Appl. 2000, EP1061103.
Representative procedure for synthesis: 1 mmol nucleophile (2, 7 or 9) was
added to 5 mL aqueous suspension of surfactant (0.5 mole % SDS). After
stirring for five minutes, quinone 1 or 5 (1 mmol) was added and stirred at
temperatures represented in Tables or Schemes. The products were filtered
and purified after neutralization with 5% HCl, followed by column
chromatography (if required) of the reaction mixture (hexane/EtOAc)
leading to desired products. 6-chlorobenzo[a]phenazin-5-ol (4a): red
powder; IR (KBr): 1597 and 1675 (>C=O), 3443 (OH) cm-1; 1H NMR (300
MHz, DMSO-d6): 7.72 (m, 1H), 7.87 (m, 3H), 8.12 (m, 2H), 8.26 (s,
1H), 8.33 (m, 1H), 9.06 (m, 1H); 13C NMR (75 MHz, DMSO-d6): 104.8,
124.6, 125.0, 125.5, 127.3, 128.1, 129.5, 129.8, 130.0, 131.0, 136.3, 137.0,
140.0, 143.9, 146.1, 167.1; m/z: 283.2 [M+H]+; Anal. Calcd. for C16H9ClN2O:
C, 68.46; H, 3.23; N, 9.98%. Found: C, 68.57; H, 3.30; N, 10.10%. Beilstein
test: Cl positive; 2-phenyl-1H-naphtho[2,3-d]imidazole-4,9-dione (8a):
dark red needles; IR (KBr): 1671 (>C=O of quinone), 3342 (NH) cm-1; 1H
NMR (300 MHz, DMSO-d6): 7.40-7.54 (m, 5H), 7.71 (m, 1H), 7.83-7.97
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
(m, 3H), 8.19 (m, 1H); 13C NMR (75 MHz, DMSO-d6): 127.5, 128.3
(2C), 129.0 (2C), 129.8 (2C), 129.9 (2C), 130.0, 130.1, 131.4, 133.6, 136.0,
166.8, 187.1 (2C); m/z: 274.8 [M]+; Anal. Calcd. for C17H10N2O2: C, 74.44; H,
3.67; N, 10.21%. Found: C, 74.28; H, 3.74; N, 10.34%.
22.
23.
24.
Kawasaki, I.; Taguchi, N.; Yamashita, M.; Ohta, S. Chem. Pharm. Bull.
1997, 45, 1393.
Nakamura, S.;Tsuno, N.; Yamashita, M.; Kawasaki, I.; Ohta, S.; Ohishi,Y.
J. Chem. Soc., Perkin Trans. 1, 2001, 429.
Nakamura, S.; Kawasaki, I.; Kunimura, M.; Matsui, M.; Noma, Y.;
Yamashita, M.; Ohta, S. J. Chem. Soc., Perkin Trans. 1, 2002, 1061.