C. S. Cho et al. / Tetrahedron Letters 48 (2007) 4665–4667
4667
Table 2. Synthesis of quinoxalines 3 from o-phenylenediamines 1 and
ketones 2a
Acknowledgement
This present work was supported by a Research Profes-
sor Grant of Kyungpook National University (2006).
1
Ketones 2
Quinoxalines 3
Isolated
yield (%)
N
Ar
O
Ar
N
Me
References and notes
1a 2a Ar = Ph
3a Ar = Ph
3b Ar = 4-OMeC6H4
3c Ar = 4-ClC6H4
72
59
54
2b Ar = 4-OMeC6H4
2c Ar = 4-ClC6H4
1. Cheeseman, G. W. H.; Cookson, R. F. In Condensed
Pyrazines; Weissberger, A., Taylor, E. C., Eds.; Wiley-
Interscience: New York, 1979.
2. For quinoxaline synthesis from 1,2-diketones and 1,2-
diamines catalyzed by cerium(IV) ammonium nitrate, see:
More, S. V.; Sastry, M. N. V.; Yao, C.-F. Green Chem.
2006, 8, 91.
3. (a) Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Chem.
Commun. 2003, 2286; (b) Raw, S. A.; Wilfred, C. D.;
Taylor, R. J. K. Org. Biomol. Chem. 2004, 2, 788.
4. Robinson, R. S.; Taylor, R. J. K. Synlett 2005, 1003.
5. Kim, S. Y.; Park, K. H.; Chung, Y. K. Chem. Commun.
2005, 1321.
N
Ph
O
R
Ph
N
R
1a 2d R = Pr
3d R = Pr
73
65
68
67
2e R = hexyl
2f R = phenethyl
2g R = Ph
3e R = hexyl
3f R = phenethyl
3g R = Ph
O
N
Ph
N
Ph
Ph
6. Marques, C. S.; Moura, N.; Burke, A. J. Tetrahedron Lett.
2006, 47, 6049.
1a 2h
3h
3i
3j
75
56
30
N
N
7. Antoniotti, S.; Dunach, E. Tetrahedron Lett. 2002, 43,
˜
O
3971.
Ph
1a 2i
8. For Isoindolinones, see: (a) Cho, C. S.; Lee, J. W.; Lee, D.
Y.; Shim, S. C.; Kim, T. J. Chem. Commun. 1996, 2115; (b)
Cho, C. S.; Shim, H. S.; Choi, H.-J.; Kim, T.-J.; Shim,
S. C.; Kim, M. C. Tetrahedron Lett. 2000, 41, 3891.
9. For indoles, see: (a) Cho, C. S.; Lim, H. K.; Shim, S. C.;
Kim, T. J.; Choi, H.-J. Chem. Commun. 1998, 995; (b)
Cho, C. S.; Kim, J. H.; Shim, S. C. Tetrahedron Lett. 2000,
41, 1811; (c) Cho, C. S.; Kim, J. H.; Kim, T.-J.; Shim, S. C.
Tetrahedron 2001, 57, 3321; (d) Cho, C. S.; Kim, J. H.;
Choi, H.-J.; Kim, T.-J.; Shim, S. C. Tetrahedron Lett.
2003, 44, 2975.
N
N
O
1a 2j
N
N
O
10. For quinolines, see: (a) Cho, C. S.; Oh, B. H.; Shim, S. C.
Tetrahedron Lett. 1999, 40, 1499; (b) Cho, C. S.; Oh, B.
H.; Shim, S. C. J. Heterocycl. Chem. 1999, 36, 1175; (c)
Cho, C. S.; Kim, J. S.; Oh, B. H.; Kim, T.-J.; Shim, S. C.
Tetrahedron 2000, 56, 7747; (d) Cho, C. S.; Oh, B. H.;
Kim, J. S.; Kim, T.-J.; Shim, S. C. Chem. Commun. 2000,
1885; (e) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C.
Chem. Commun. 2001, 2576; (f) Cho, C. S.; Kim, T. K.;
Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Organomet. Chem.
2002, 650, 65; (g) Cho, C. S.; Kim, B. T.; Choi, H.-J.;
Kim, T.-J.; Shim, S. C. Tetrahedron 2003, 59, 7997; (h)
Cho, C. S. J. Organomet. Chem. 2005, 690, 4094; (i) Cho,
C. S.; Ren, W. X.; Shim, S. C. Tetrahedron Lett. 2006, 47,
6781.
11. For indazoles and pyrazoles, see: (a) Cho, C. S.; Lim, D.
K.; Heo, N. H.; Kim, T.-J.; Shim, S. C. Chem. Commun.
2004, 104; (b) Cho, C. S.; Patel, D. B. Tetrahedron 2006,
62, 6388.
12. Cho, C. S.; Oh, S. G. Tetrahedron Lett. 2006, 47,
5633.
13. For poly(ethylene glycol) (PEG) as a recyclable medium
along with a transition metal catalyst, see: (a) Chan-
drasekhar, S.; Narsihmulu, Ch.; Sultana, S. S.; Reddy,
N. R. Org. Lett. 2002, 4, 4399; (b) Heldebrant, D. J.;
Jessop, P. G. J. Am. Chem. Soc. 2003, 125, 5600; (c) Li,
J.-H.; Zhu, Q.-M.; Liang, Y.; Yang, D. J. Org. Chem.
2005, 70, 5347; (d) Li, J.-H.; Liu, W.-J.; Xie, Y.-X. J.
Org. Chem. 2005, 70, 5409; (e) Mai, W.; Gao, L. Synlett
2006, 2553; (f) Wang, L.; Zhang, Y.; Liu, L.; Wang, Y.
J. Org. Chem. 2006, 71, 1284; (g) Chandrasekhar, S.;
Sultana, S. S.; Yaragorla, S. R.; Reddy, N. R. Synthesis
2006, 839.
1a 2k
3k
3l
31
51
61
O
N
N
1a 2l
O
N
N
1a 2m
3m
Me
N
N
Me
Ar
1b 2a
2b
2c
3n Ar = Ph
3o Ar = 4-OMeC6H4
3p Ar = 4-ClC6H4
54
74
49
Me
N
N
Ph
Ph
Me
1b 2g
3q
71
95
Me
N
N
Me
Ph
1b 2h
3r
a Reaction conditions: 1 (1 mmol), 2 (2 mmol), KOH (3 mmol), PEG-
400 (2 mL), 60 °C, 60 h.