264
X. Qi et al. / Tetrahedron Letters 49 (2008) 261–264
used in this report) were failed when fluorophore exists. So
References and notes
we turned to search for other more reliable ways (as
reported herein) to fulfill the desired structure diversity.
1
. Haugland, R. P. Handbook of Fluorescent Probes and
Research Chemicals, 9th ed.; Molecular Probes: Eugene,
Oregon, 2002.
8
. Compound 1: as red solid (135.8 mg, 0.192 mmol, 32.0%):
1
mp 235–236 °C. H NMR (CDCl
3
): d 1.33 (s, 6H), 2.54 (s,
6
7
1
H), 4.85 (s, 2H), 4.98 (s, 2H), 5.94 (s, 2H), 7.01 (m, 1H),
.13–7.27 (m, 10H), 7.45 (m, 2H), 7.57 (m, 2H), 8.48 (d,
H, J = 3.6 Hz), 8.54 (d, 1H, J = 3.6 Hz). C NMR
): d 14.4, 14.5, 52.1, 120.3, 121.2, 121.4, 121.6,
2
. Ziessel, R.; Ulrich, G.; Harriman, A. New J. Chem. 2007,
31, 496, and references cited therein.
13
3
. (a) Rurack, K.; Kollmannsberger, M.; Resch-Genger, U.;
Daub, J. J. Am. Chem. Soc. 2000, 122, 968; (b) Turfan, B.;
Akkaya, E. U. Org. Lett. 2002, 4, 2857; (c) Moon, S. Y.;
Cha, N. R.; Kim, Y. H.; Chang, S.-K. J. Org. Chem. 2004,
(
CDCl
3
1
1
1
22.2, 122.3, 122.8, 123.3, 128.7, 131.4, 131.6, 136.5, 136.6,
38.2, 140.8, 143.0, 149.3, 149.4, 152.8, 155.5, 166.2, 167.5,
+
71.4. HRMS (FAB) m/z 708.3194 (M+H) , calcd for
69, 181; (d) Yamada, K.; Nomura, Y.; Citterio, D.;
C H37BF N O: 708.3189; Compound 2: as red solid
40 2 9
Iwasawa, N.; Suzuki, K. J. Am. Chem. Soc. 2005, 127,
1
(
117 mg, 0.15 mmol, 26%): mp 98 °C. H NMR (CDCl ):
d 1.33 (s, 6H), 2.55 (s, 6H), 4.85 (s, 2H), 4.97 (s, 2H), 5.95
s, 2H), 7.16–7.37 (m, 12H), 7.58 (m, 2H), 8.57 (dd, 2H,
6956; (e) Coskun, A.; Akkaya, E. U. J. Am. Chem. Soc.
3
2005, 127, 10464; (f) Qi, X.; Jun, E. J.; Xu, L.; Kim, S.-J.;
(
Hong, J. S. J.; Yoon, Y. J.; Yoon, J. J. Org. Chem. 2006,
1, 2881; (g) Yu, Y.-H.; Descalzo, A. B.; Shen, Z.; R o¨ hr,
1
3
J = 20.6, 4.2 Hz). C NMR (CDCl
3
): d 14.4, 14.5, 52.2,
21.3, 121.7, 122.4, 122.8, 128.3, 128.7, 128.8, 131.4, 131.8,
36.6, 136.8, 143.0, 149.4, 152.7, 155.6, 157.0. HRMS
7
1
1
(
H.; Liu, Q.; Wang, Y.-W.; Spieles, M.; Li, Y.-Z.; Rurack,
K.; You, X.-Z. Chem. Asian. J. 2006, 1–2, 176; (h)
Coskun, A.; Akkaya, E. U. J. Am. Chem. Soc. 2006, 128,
+
FAB) m/z 742.2766 (M+H) , calcd for
40 36
C H -
BClF N O: 742.2800; Compound 3: as red solid (106 mg,
14474; (i) Mei, Y.; Bentley, P. A.; Wang, W. Tetrahedron
2
9
1
0
1
2
.144 mmol, 24.0%) mp: 138–140 °C. H NMR (CDCl ): d
.32 (s, 6H), 2.54 (s, 6H), 3.75 (s, 3H), 4.83 (s, 2H), 4.94 (s,
H), 5.94 (s, 2H), 6.73 (m, 2H), 7.12–7.40 (m, 10H), 7.56
Lett. 2006, 47, 2447; (j) Kim, H. J.; Kim, J. S. Tetrahedron
Lett. 2006, 47, 7051; (k) Peng, X.; Du, J.; Fan, J.; Wang,
J.; Wu, Y.; Zhao, J.; Sun, S.; Xu, T. J. Am. Chem. Soc.
3
(
m, 2H), 8.47 (d, 1H, J = 3.8 Hz), 8.54 (d, 1H, J = 3.8 Hz).
C NMR (CDCl ): d 14.4, 14.5, 52.0, 55.4, 113.8, 121.2,
3
2007, 129, 1500.
1
3
4
5
6
. Baruah, M.; Qin, W.; Basari c´ , N.; De Borggaeve, W. M.;
Boens, N. J. Org. Chem. 2005, 70, 4152.
. Gabe, Y.; Urano, Y.; Kikuchi, K.; Kojima, H.; Nagano,
T. J. Am. Chem. Soc. 2004, 126, 3357.
1
1
21.4, 121.6, 122.1, 122.3, 122.4, 122.8, 131.2, 131.4, 131.5,
36.4, 140.8, 143.0, 149.2, 152.8, 155.5, 155.9, 157.2.
+
HRMS (FAB) m/z 738.3291 (M+H) , calcd for C H -
41 39
BF
2
N
9
O
2
738.3295; Compound 4: as red solid (112.6 mg,
. (a) Steffensen, M. B.; Simanek, E. E. Org. Lett. 2003, 5,
1
0
.15 mmol, 25%): mp 146–148 °C. H NMR (CDCl
3
): d
2359–2361; (b) L o¨ wik, D. W. P. M.; Lowe, C. R. Eur. J.
1
.32 (s, 6H), 2.54 (s, 6H), 2.88 (s, 6H), 4.83 (s, 2H), 4.96
Org. Chem. 2001, 2825; (c) Wang, M. X.; Yang, H. B. J.
Am. Chem. Soc. 2004, 126, 15412; (d) Scharn, D.;
Wenschuh, H.; Reineke, U.; Schneider-Mergener, J.;
Germeroth, L. J. Comb. Chem. 2000, 2, 361.
(
7
s, 2H), 5.86 (s, 2H), 6.60 (m, 2H), 7.01–7.27 (m, 10H),
.56 (m, 2H), 8.48 (d, 1H, J = 3.8 Hz), 8.54 (d, 1H,
1
3
J = 4.1 Hz). C NMR (CDCl
1
1
3
): d 14.4, 14.5, 40.9, 51.9,
12.9, 121.2, 121.5, 122.1, 122.4, 122.8, 128.6, 131.4, 136.4,
40.9, 143.0, 147.5, 149.2, 152.8, 155.4, 157.4. HRMS
7
. R o¨ hr, H.; Trieflinger, C.; Rurack, K.; Daub, J. Chem. Eur.
J. 2006, 12, 689. During our data processing, the Daub
group reported a BODIPY structure containing a mono-
substituted triazine structure via a condensation reaction
between a BODIPY dye bearing a thiol group and
cyanuric chloride. Indeed, we first adopted the same
methodology in our studies (hydroxyl in the case instead
of thiol), but only the abovementioned mono-substituted
derivative was obtained successfully through that type of
direct condensation involving in the most reactive chlorine
atom of cyanuric chloride. Subsequent substitutions of the
second and third chlorine atoms on the triazine core from
the mono-substituted structure by nucleophiles (ligands
+
(
2
FAB) m/z 750.3528 (M+H) , calcd for C42H41BF N10O:
7
50.3533.
9
. (a) Burghart, A.; Kim, H.; Welch, M. B.; Thoresen, L. H.;
Reibenspies, J.; Burgess, K.; Bergstr o¨ m; Johansson, L. B.-
A. J. Org. Chem. 1999, 64, 7813; (b) Lai, R. Y.; Bard, A. J.
J. Phys. Chem. B 2003, 107, 5036.
0. (a) Malval, J. P.; Morand, J. P.; Lapouyade, R.; Rettig,
W.; Jonusauskas, G.; Oberl e´ , J.; Trieflinger, C.; Daub, J.
Photochem. Photobiol. Sci. 2004, 3, 939; (b) Kollmanns-
berger, M.; Gareis, T.; Heinl, S.; Breu, J.; Daub, J. Angew.
Chem., Int. Ed. 1997, 36, 1333.
1