238
L. Lista et al. / Tetrahedron 64 (2008) 234e239
2
1
(
MeOH) 302 nm; IR n
(CHCl ) 3474, 1554, 1440, 1427,
3
4.2.12. 8-Hydroxy-5,7-diiodoquinoline (10b)
max
ꢁ
1
1
327, 1296 cm ; H NMR (CDCl ) d (ppm) 7.93 (1H, s);
ꢀ
15a
1
Greenish powder; mp 206e210 C (lit.
þ
mp 214e
215 C); ESI(þ) MS m/z 398 [MþH] ; ESI-HRMS calculated
3
1
3
ꢀ
C NMR (CDCl ) d (ppm) 71.7 (C), 145.2 (CH), 155.0 (C).
3
þ
for C H NOI [MþH] : 397.8539, found 397.8544; UV l
9
6
2
max
4
g
4
.2.7. 1-Iodo-2-naphthol (5b)
(MeOH) 260, 335 nm; IR n
(CHCl ) 2940, 1480, 1450,
3
max
ꢁ
ꢁ1
1
1380, 1330, 1200 cm ; H NMR (CD OD) d (ppm) 7.53
Brown oil; ESI(ꢁ) MS m/z 269 [MꢁH] ; ESI-HRMS cal-
3
ꢁ
culated for C H OI [MꢁH] : 268.9463, found 268.9428; UV
(1H, dd, J 8.4, 8.7 Hz), 8.25 (1H, dd, J 8.4, 1.5 Hz), 8.32
1
0 6
1
3
l
3
1
(MeOH) 280, 320, 330, 360 (s) nm; IR n (CHCl )
500, 3380, 2940, 1620, 1600, 1470, 1380, 1220, 1170,
(1H, s), 8.80 (1H, dd, J 8.7, 1.5 Hz); C NMR (DMSO-d6)
d (ppm) 80.8 (C), 85.2 (C), 124.2 (CH), 129.6 (C), 138.0
(C), 140.0 (CH), 144.6 (CH), 149.6 (CH), 154.8 (C).
max
max
3
ꢁ
1
;
1
150 cm
H NMR (acetone-d ) d (ppm) 7.29 (1H, d,
6
J 9.0 Hz), 7.37 (1H, t, J 7.2 Hz), 7.56 (1H, t, J 7.2 Hz), 7.81
1H, d, J 8.1 Hz), 7.82 (1H, d, J 9.0 Hz), 8.06 (1H, d,
(
2
2
1
3
4.2.13. 2,4,5-Triiodoimidazole (11b)
J 8.1 Hz), 9.52 (1H, s); C NMR (acetone-d ) d (ppm) 94.3
6
ꢁ
Yellowish oil; ESI(ꢁ) MS m/z 445 [MꢁH] ; ESI-HRMS
(
(
C), 117.4 (CH), 123.0 (CH), 124.9 (CH), 128.2 (CH), 128.6
CH), 129.9 (C), 130.5 (CH), 137.7 (C), 152.36 (C).
ꢁ
calculated for C N I [MꢁH] : 444.7196, found 444.7195;
3
2 3
1
3
C NMR (CD OD) d (ppm) 89.0 (C).
3
2
4
4
.2.8. 2,4-Diiodoaniline (6b)
ꢀ
24
ꢀ
Dark powder; mp 94e96 C (lit. mp 93 C); ESI(þ) MS
Acknowledgements
þ
m/z 346 [MþH] ; ESI-HRMS calculated for C H NI
6
6
2
þ
[
MþH] : 345.8590, found 345.8596; UV l
(MeOH) 250,
(CHCl ) 3480, 3393, 1610, 1470, 1380 cm
This work was carried out in the frame of a program spon-
sored by MIUR (PRIN 2006). We thank the ‘Centro Interdi-
partimentale di Metodologie Chimico-Fisiche’ (CIMCF,
University of Naples Federico II) for NMR and mass spec-
trometry facilities. The technical assistance of Mrs. Silvana
Corsani is gratefully acknowledged.
max
ꢁ
1
3
05 nm; IR n
;
H NMR (CD OD) d (ppm) 6.57 (1H, d, J 8.2 Hz), 7.33 (1H,
max
3
1
3
1
dd, J 8.2, 2.0 Hz), 7.80 (1H, d, J 2.0 Hz); C NMR (CD OD)
3
3
d (ppm) 78.6 (C), 85.2 (C), 117.9 (CH), 139.3 (CH), 147.2
(CH), 149.8 (C).
2
0
4
.2.9. 2-Iodo-4-nitroaniline (7b)
ꢀ
25
Orange powder; mp 96e98 C (lit. mp 106e107 C);
ꢀ
References and notes
þ
þ
ESI(þ) MS m/z 265 [MþH] , 287 [MþNa] ; ESI-HRMS cal-
1
. (a) Kung, H. F.; Newman, S.; Choi, S.-R.; Oya, S.; Hou, C.; Zhuang, Z.-P.;
Acton, P. D.; Ploessl, K.; Winkler, J.; Kung, M.-P. J. Med. Chem. 2004, 47,
5258e5264; (b) Bennacef, I.; Tymciu, S.; Dhilly, M.; Lasne, M.-C.;
Debruyne, D.; Perrio, C.; Barre, L. Bioorg. Med. Chem. 2004, 12,
þ
culated for C H N O I [MþH] : 264.9474, found 264.9470;
6
6 2 2
UV l
1
(MeOH) 270, 360 nm; IR n
(CHCl ) 3390, 2940,
max
max 3
ꢁ
640, 1600, 1515, 1470, 1330 cm ; H NMR (CD OD)
3
1
1
4
533e4541.
2. Dunn, A. D.; Corsi, C. M.; Myers, H. E.; Dunn, J. T. J. Biol. Chem. 1998,
73, 25223e25229.
d (ppm) 6.70 (1H, d, J 8.7 Hz), 8.04 (1H, dd, J 8.7, 2.4 Hz),
8
1
.54 (1H, d, J 2.4 Hz); C NMR (CD OD) d (ppm) 80.2 (C),
3
3
2
1
13.5 (CH), 127.0 (CH), 137.1 (CH), 139.6 (C), 156.5 (C).
3
. (a) Orito, K.; Hatakeyama, T.; Takeo, M.; Suginome, H.; Tokuda, M. Syn-
thesis 1997, 23e25; (b) Yang, S. G.; Kim, Y. H. Tetrahedron Lett. 1999,
40, 6051e6054; (c) Blackmore, I. J.; Boa, A. N.; Murray, E. J.; Dennis,
M.; Woodward, S. Tetrahedron Lett. 1999, 40, 6671e6672; (d) Olah,
G. A.; Wang, Q.; Sandford, G.; Surya Prakash, G. K. J. Org. Chem.
4
.2.10. 5,6-Diacetoxy-2,3-diiodoindole (8b)
ꢀ
Needles from ethanol; mp dec >80 C; ESI(þ) MS m/z 486
þ
þ
[
4
MþH] ; ESI-HRMS calculated for C H NO I [MþH] :
1
2
10
4 2
1
993, 58, 3194e3195; (e) Carreno, M. C.; Garcia Ruano, J. L.; Sanz,
85.8699, found 485.8705; UV l
(MeOH) 304 nm; IR
;
max
G.; Toledo, M. A.; Urbano, A. Tetrahedron Lett. 1996, 37, 4081e4084;
(f) Mukaiyama, T.; Kitagawa, H.; Matsuo, J.-I. Tetrahedron Lett. 2000,
41, 9383e9386; (g) Sathiyapriya, R.; Karunakaran, R. J. J. Chem. Res.
ꢁ1
1
nmax 1769, 1602, 1444, 1371, 1319 cm
H NMR
(
H-7), 7.31 (1H, s, H-4), 11.29 (1H, s, NH); C NMR (ace-
CD OD) d (ppm) 2.29 (6H, s, 2ꢂOCOCH ), 7.15 (1H, s,
3
3
1
3
2
006, 575e576; (h) Barluenga, J.; Alvarez-Gutierrez, J. M.; Ballesteros,
A.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2007, 46, 1281e1283.
. (a) Narender, N.; Srinivasu, P.; Kulkarni, S. J.; Raghavan, K. V. Synth.
Commun. 2002, 32, 2319e2324; (b) Das, B.; Holla, H.; Srinivas, Y.;
Chowdhury, N.; Bandgar, B. P. Tetrahedron Lett. 2007, 48, 3201e3204;
tone-d ) d (ppm) 21.2 (2ꢂCOCH ), 71.2 (C), 90.0 (C),
6
3
4
1
1
06.1 (CH), 114.4 (CH), 129.4 (C), 136.6 (C), 138.4 (C),
39.9 (C), 168.8 (OCOCH ), 168.9 (OCOCH ).
3
3
(
c) Brazdil, L. C.; Fitch, J. L.; Cutler, C. J.; Haynik, D. M.; Ace, E. R.
J. Chem. Soc., Perkin Trans. 2 1998, 933e936; (d) Sy, W.-W. Tetrahedron
Lett. 1993, 34, 6223e6224; (e) Kraszkiewicz, L.; Sosnowski, M.; Skulski,
L. Synthesis 2006, 1195e1199; (f) Suzuki, H. Bull. Chem. Soc. Jpn. 1971,
4
.2.11. 3-Iodo-5-nitroindole (9b)
ꢀ
Light yellow crystals (ethanol); mp 167e170 C; ESI(þ) MS
þ
þ
m/z 289 [MþH] , 311 [MþNa] ; ESI-HRMS calculated for
4
4, 2871e2873; (g) Edgar, K. J.; Falling, S. N. J. Org. Chem. 1990, 55,
þ
C H N O I [MþH] : 288.9474, found 288.9479; UV l
8
6
2
2
max
1
5287e5291; (h) Pavlinac, J.; Zupan, M.; Stavber, S. Org. Biomol.
Chem. 2007, 5, 699e707; (i) Patil, B. R.; Bhusareb, S. R.; Pawar, R. P.;
Vibhute, Y. B. Tetrahedron Lett. 2005, 46, 7179e7181; (j) Das, B.; Krish-
naiah, M.; Venkateswarlu, K.; Reddy, V. S. Tetrahedron Lett. 2007, 48,
ꢁ
1622, 1525, 1472, 1341 cm ;
max
(
MeOH) 269, 319 nm; IR n
H NMR (CD OD) d (ppm) 7.51 (1H, d, J 9.0 Hz), 7.56 (1H,
3
1
d, J 2.2 Hz), 8.05 (1H, dd, J 9.0, 2.2 Hz), 8.24 (1H, d, J
8
1e83.
1
.1 Hz); C NMR (CD OD) d (ppm) 58.9 (C), 113.7 (CH),
18.8 (CH), 119.2 (CH), 131.4 (C), 134.9 (CH), 141.4 (C),
43.9 (C).
3
2
1
1
3
5
. Fernlund, P.; Gershagen, S. J. Steroid Biochem. 1990, 36, 75e81.
. (a) Numazawa, M.; Ogura, Y. J. Chem. Soc., Chem. Commun. 1983, 533e
534; (b) Mohanakrishnan, A. K.; Cushman, M. Synlett 1999, 1097e1099.
6