2,4-Ddiamino-6-piperidino-1,3,5-triazine, 3i. Synthesized
from cyanopiperidine (1.44 g, 15 mmol). The diaminotriazine
5
6
7
L. Brunsveld, J. A. J. M. Vekemans, J. H. K. K. Hirschberg, R. P.
Sijbesma and E. W. Meijer, Proc. Natl. Acad. Sci. U. S. A., 2002,
9, 4977.
(a) L. J. Prins, D. N. Reinhoudt and P. Timmerman, Angew.
Chem., Int. Ed., 2001, 40, 2382; (b) E. A. Archer, H. C. Gong
and M. J. Krische, Tetrahedron, 2001, 57, 1139.
(a) M. Mascal, J. Hansen, P. S. Fallon, A. J. Blake, B. R.
Heywood, M. H. Moorea and J. P. Turkenburg, Chem.-Eur. J.,
1999, 5, 381; (b) Y. W. Cao, X. D. Chai, T. J. Li, J. Smith and
D. Li, Chem. Commun., 1999, 1605.
9
was washed with dichloromethane (5 mL) and dried. Yield
ꢂ
2
.57 g (88%), mp 221–223 C. IR (KBr) 3497, 3427, 1616
NH) and (n
1
(n
C
=
N
). H-NMR (DMSO) d 1.3–1.45 (m, 4H, H
3
and H ), 1.5–1.6 (m, 2H, H
5
4
), 3.59 (t, J 5.2, 4H, H
2
and H
). C-NMR (DMSO) d 25.17 (C
), 43.94 (C and C ), 165.73 (C
). Anal. Calcd. for C : C, 49.47; H, 7.26;
N, 43.27. Found: C, 49.18; H, 8.67; N, 43.74. MS (EI) m/z
94.13 (M).
6
),
),
1
3
6
2
.05 (br s, 4H, NH
6.13 (C and C
and C
2
0
4
0
0
0
0
6
), 167.89
3
5
2
6
(
C
2
4
8 14 6
H N
8
9
V. Paraschiv, M. Crego-Calama, R. H. Fokkens, C. J. Padberg,
P. Timmerman and D. N. Reinhoudt, J. Org. Chem., 2001, 66,
1
8
297.
L. J. Prins, R. Hulst, P. Timmerman and D. N. Reinhoudt, Chem.
Eur. J., 2002, 8, 2288.
2,4-Diamino-6-morpholino-1,3,5-triazine, 3j. Prepared from
cyanomorpholine (1.68 g, 15 mmol). The diaminotriazine
-
10 (a) D. C. Sherrington and K. A. Taskinen, Chem. Soc. Rev., 2001,
30, 83; (b) R. P. Sijbesma and E. W. Meijer, Chem. Commun.,
2003, 5.
11 H. Sauriat-Dorizon, T. Maris, J. D. Wuest and G. D. Enright,
J. Org. Chem., 2003, 68, 240.
was washed with dichloromethane (5 mL) and dried. Yield
ꢂ
2
.09 g (71%), mp 221–223 C. IR (KBr) 3497, 3427, 1660
NH) and (n
1
(n
C
=
N
). H-NMR (DMSO) d 3.5–3.6 (m, 8H, mor-
13
pholine-H), 6.14 (br s, 4H, NH2). C-NMR (CDCl ) d 41.04
(C
and C ). Anal. Calcd. for C H N O: C, 42.85; H, 6.16; N,
3
1
2
A. D. Burrows, C.-W. Chan, M. M. Chowdhry, J. E. McGrady
and D. M. P. Mingos, Chem. Soc. Rev., 1995, 329.
0
and C
6 3 5 6 2
), 66.75 (C and C ), 166.15 (C ), 167.83 (C
0 0 0
2
4
7
12
6
13 (a) C. R. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48,
1665; (b) L. Perreux and A. Loupy, Tetrahedron, 2001, 57, 9199;
4
1
2.83. Found: C, 42.94; H, 5.93; N, 42.84. MS (EI) m/z
96.11 (M).
(c) P. Lidstr o¨ m, J. Tierney, B. Wathey and J. Westman, Tetra-
hedron, 2001, 57, 9225.
1
4
(a) A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault
and D. Math e´ , Synthesis, 1998, 1213; (b) R. S. Varma, Green
Chem., 1999, 1, 43.
1
,2-Bis(2,4-diamino-1,3,5-triazin-6-yl)benzene, 5. Formed
from 1,2-dicyanobenzene (1.92 g, 15 mmol). The diamino-
triazine was washed with acetone (5 mL) and dried. Yield
.54 g (80%), mp > 270 C. IR (KBr) 3465, 3456, 1394 (nNH
15 P. T. Anastas and J. C. Warner, Green Chemistry: Theory and
Practice, Oxford University Press, New York, 1998.
16 C.-W. Chan, D. M. P. Mingos, A. J. P. White and D. J. Williams,
Polyhedron, 1996, 15, 1753.
ꢂ
3
)
1
and (n
C
=
N
0
). H-NMR (DMSO) d 6.34–6.52 (br s, 8H, NH
2
),
0
0
0
7
.44 (AA XX , J 7.8, 6.7, 1.4, 2H, H
2
0
and H
5
0
), 7.60 (AA XX ,
1
7
J. Catal a´ n, J. L. M. Abboud and J. Elguero, Adv. Heterocycl.
Chem., 1987, 41, 187.
G. Rothenberg, A. P. Downie, C. L. Raston and J. L. Scott, J. Am.
Chem. Soc., 2001, 123, 8701.
1
3
J 7.8, 6.7, 1.4, 2H, H
3
0
and H
), 129.30 (C and C
C ), 166.80 (C2 and C ). Anal. Calcd. for C H N : C,
4
0
). C-NMR (DMSO) d 128.36
), 138.66 (C and C ), 173.90
(
(
C
3
0
and C
6
0
4
0
5
0
1
0
0
2
1
8
6
4
12 12 10
48.64; H, 4.08; N, 47.27. Found: C, 47.47, H; 4.06, N; 45.95.
MS (EI) m/z 296.00 (M).
19 (a) I. Ghiviriga and D. C. Oniciu, Chem. Commun., 2002, 2718; (b)
A. D ´ı az-Ortiz, J. Elguero, C. Foces-Foces, A. de la Hoz, A.
Moreno, S. Moreno, A. S a´ nchez-Migall o´ n and G. Valiente,
Org. Biomol. Chem., 2003, 1, 4451.
2
0
H. E. Birkett, J. C. Cherryman, A. M. Chippendale, J. S. O.
Evans, R. K. Harris, M. James, I. J. King and G. J. McPherson,
Magn. Reson. Chem., 2003, 41, 324.
Acknowledgements
Financial support from the DGICYT of Spain through
projects BQU2000-0868 and BQU2001-1095 and from the
Consejer ´ı a de Ciencia y Tecnolog ´ı a JCCM through project
PAI-02-019 is gratefully acknowledged. CFF thanks Professor
M. L. Rodriguez (La Laguna University, Spain) for the use of
the CCD diffractometer.
2
1
J. Sandstr o¨ m, in Dynamic NMR Spectroscopy, Academic Press,
New York, 1982.
22 F. H. Allen, J. E. Davies, J. J. Galloy, O. Johnson, O. Kennard,
C. F. Macrae, E. M. Mitchell, J. F. Mitchell, J. M. Smith and
D. G. Watson, J. Chem. Inf. Comput. Sci., 1991, 31, 187.
2
3
Z. Otwinowski and W. Minor, in Methods in Enzymology, eds.
C. E. Carter and R. M. Sweet, Academic Press, London, 1997,
vol. 276, pp. 307–326.
2
2
4
5
COLLECT, Nonius Kappa CCD Server Software, Nonius B. V.,
Delft, The Netherlands, 1998.
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C.
Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori and
R. Spagna, J. Appl. Crystallogr., 1999, 32, 115.
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T h i s j o u r n a l i s Q T h e R o y a l S o c i e t y o f C h e m i s t r y a n d t h e
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