4
16
H. C. Ma, X. Z. Jiang
PAPER
1
MS (FAB): m/z = 212.8 [M + H+].
Anal. Calcd for C H N : C, 67.90; H, 5.70; N, 26.40. Found: C,
H NMR (400 MHz, CDCl ): d = 7.62 (d, J = 5.0 Hz, 1 H), 7.30 (t,
3
J = 5.3 Hz, 1 H), 7.03 (t, J = 5.0 Hz, 1 H), 6.86 (d, J = 6.3 Hz, 1 H),
6
1
2
12
4
.74 (d, J = 4.5 Hz, 1 H), 6.45 (d, J = 6.5 Hz, 1 H), 5.12 (s, 2 H).
6
7.78; H, 5.59; N, 26.24.
1
3
C NMR (100 MHz, CDCl ): d = 180.03, 153.66, 148.39, 142.92,
3
1
32.98, 129.47, 129.43, 127.63, 126.02, 121.21, 114.79, 104.36.
Acknowledgment
MS (FAB): m/z = 356.8 [M + H+].
We are grateful to the financial support of the National Natural
Science Foundation of China (no.20376071). We also thank Dr.
Zhanxiang Liu and Dr. Yongbao Zhu for fruitful discussion.
Anal. Calcd for C H Br N O: C, 40.48; H, 2.26; N, 7.87. Found: C,
12
8
2
2
4
0.32; H, 2.38; N, 7.62.
2
-Amino-5-bromo-(1,4)-benzoquinone-4-(4-bromo)phenylim-
ide (8b)
References
Bright red-orange solid; mp >300 °C.
(
1) For selected reviews, see: (a) Morales-Rojas, H.; Moss, R.
A. Chem. Rev. 2002, 102, 2497. (b) Zhdankin, V. V.; Stang,
P. J. Chem. Rev. 2002, 102, 2523. (c) Stang, P. J.;
IR (KBr): 3477, 3375, 1648, 1621, 1582, 1477, 1218, 1065, 1002,
–1
8
75, 833 cm .
1
H NMR (400 MHz, CDCl ): d = 7.48 (d, J = 5.3 Hz, 2 H), 7.19 (s,
3
Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
1
H), 6.73 (d, J = 5.5 Hz, 2 H), 5.88 (s, 1 H), 4.66 (s, 2 H).
(
2) (a) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong,
Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. (b) Thottumkara,
A. P.; Bowsher, M. S.; Vinod, T. K. Org. Lett. 2005, 7, 2933.
3) Jarugu, N. M.; Nidhi, S.; Kalyan, S. Tetrahedron Lett. 2006,
1
3
C NMR (100 MHz, CDCl ): d = 180.82, 154.77, 149.28, 143.27,
3
1
42.88, 133.57, 131.92, 121.53, 117.94, 95.86.
(
MS (FAB): m/z = 356.8 [M + H+].
47, 1757.
Anal. Calcd for C H Br N O: C, 40.48; H, 2.26; N, 7.87. Found: C,
12
8
2
2
(4) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am.
Chem. Soc. 2004, 126, 5192.
4
0.31; H, 2.31; N 7.72.
(
5) Wu, Y.; Huang, J.-H.; Hu, Q.; Tang, C.-J.; Li, L. Org. Lett.
002, 4, 2141.
(6) (a) Stefan, F. K. J. Org. Chem. 2005, 70, 10210.
b) Benedikt, C.; Stefan, F. K. Chem. Commun. 2006, 764.
2
-Amino-5-iodo-(1,4)-benzoquinone-4-(4-iodo)phenylimide
2
(
9b)
Bright red-orange solid; mp >300 °C.
(
(
7) Orlando, C.; Gaetano, C.; Adele, B.; Vincenzo, P.;
IR (KBr): 3469, 3366, 1648, 1612, 1581, 1468, 1411, 1296, 1215,
–
1
Michelangelo, P.; Vincenzo, B. Org. Biomol. Chem. 2004, 2,
9
98, 872, 833 cm .
1577.
1
H NMR (400 MHz, CDCl ): d = 7.68 (d, J = 5.3 Hz, 2 H), 7.58 (s,
3
(
8) Chabner, B. A.; Allegra, C. J.; Curt, G. A.; Calabresi, P. In
Goodman and Gilman’s: The Pharmacological Basis of
Therapeutics, 9th ed.; Hardman, J. G.; Limbird, L. E.;
Molinoff, P. B.; Ruddon, R. W.; Gilman, A. G., Eds.;
McGraw-Hill: New York, 1996, 1233.
9) Delfourne, E.; Darro, F.; Bontem-Subielos, N.;
Decaestecker, C.; Bastide, J.; Frydman, A.; Kiss, R. J. Med.
Chem. 2001, 44, 3275.
1
H), 6.61 (d, J = 5.3 Hz, 2 H), 5.91 (s, 1 H), 4.58 (s, 2 H).
1
3
C NMR (100 MHz, CDCl ): d = 180.46, 155.18, 150.30, 143.34,
3
1
41.48, 138.25, 126.67, 122.47, 94.86, 88.84.
MS (FAB): m/z = 450.8 [M + H+].
(
Anal. Calcd for C H I N O: C, 32.03; H, 1.79; N, 6.23. Found: C,
1
2
8 2
2
3
2.00; H, 1.65; N, 6.18.
(
10) (a) Simándi, L. I.; Németh, S.; Rumelis, N. J. Mol. Catal.
1
-Amino-5-aza-10,11-dithiadibenzo[a,d]cyclohepten-2-one
1
987, 42, 357. (b) Simándi, L. I.; Barna, T. M.; Korecz, L.
(
10b)
Tetrahedron Lett. 1992, 34, 717.
Purple solid; mp 157–159 °C.
(
(
11) Du, Y.; Zhang, J. Chem. J. Chin. Univ. 1995, 16, 715.
12) Ikekawa, T.; Uehara, N.; Okuda, T. Chem. Pharm. Bull.
1968, 16, 1705.
IR (KBr): 3465, 3359, 1647, 1602, 1584, 1450, 1432, 1294, 1215,
8
–
1
72, 833, 678 cm .
(13) Vidyanand, G. S.; Paresh, D. S.; Krishnacharya, G. A. J.
Org. Chem. 2003, 68, 5422.
1
H NMR (400 MHz, CDCl ): d = 7.56 (d, J = 8.0 Hz, 1 H), 7.39–
3
7
.43 (m, 2 H), 7.18 (d, J = 10.0 Hz, 1 H), 7.10 (t, J = 7.6, 7.2 Hz, 1
(14) (a) Kumar, G. S.; Neckers, D. C. Chem. Rev. 1989, 89,
H), 6.63 (d, J = 10.0 Hz, 1 H), 5.21 (s, 2 H).
1915. (b) Muraoka, T.; Kinbara, K.; Kobayashi, Y.; Aida, T.
1
3
C NMR (100 MHz, CDCl ): d = 180.43, 155.71, 149.47, 149.12,
J. Am. Chem. Soc. 2003, 125, 5612. (c) Saiki, Y.; Sugiura,
H.; Nakamura, K.; Yamaguchi, M.; Hoshi, T.; Anzai, J. J.
Am. Chem. Soc. 2003, 125, 9268.
3
1
41.90, 134.83, 133.52, 131.45, 129.95, 128.25, 126.89, 109.13.
MS (FAB): m/z = 260.8 [M + H+].
(
15) (a) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew.
Chem. Int. Ed. 2000, 39, 625; Angew. Chem. 2000, 112,
Anal. Calcd for C H N OS : C, 55.36; H, 3.10; N, 10.76. Found:
C, 55.31; H, 2.89; N, 10.43.
12
8
2
2
639. (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L. J. Am.
Chem. Soc. 2001, 123, 3183. (c) Nicolaou, K. C.; Baran, P.
S.; Kranich, R.; Zhong, Y.-L.; Sugita, K.; Zou, N. Angew.
Chem. Int. Ed. 2001, 40, 202.
4
,4¢-Diazenediylbisaniline (11b)
Bright yellow solid; mp 266–268 °C.
IR (KBr): 3475, 3376, 3204, 1617, 1591, 1504, 1300, 1152, 837
cm .
(16) Gallen, M. J.; Goumont, R.; Clark, T.; Terrier, F.; Williams,
–
1
C. M. Angew. Chem. Int. Ed. 2006, 45, 2929; Angew. Chem.
2
006, 118, 2995.
17) Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem.
999, 64, 4537.
1
H NMR (400 MHz, CDCl ): d = 7.73 (d, J = 5.8 Hz, 4 H), 6.73 (d,
3
(
J = 5.3 Hz, 4 H), 3.93 (s, 4 H).
1
1
3
C NMR (100 MHz, CDCl ): d = 148.56, 145.87, 124.31, 114.73.
3
Synthesis 2007, No. 3, 412–416 © Thieme Stuttgart · New York