PAPER
Novel Chemoselective Annulation of Imidazole and 1,2,4-Thiadiazine Rings on Azoles
1081
Table 2 IR, NMR and Mass Spectral Data for Compounds 2–5 (continued)
Product IR (KBr)
(cm–1)
1H NMR (DMSO-d6/TMS)
δ, J (Hz)
13C NMR
(DMSO- d6/TMS) δ
MS
m/z (M+)
2da
3308, 3052, 2955,
2.63 (s, 3 H, Me), 3.71 (dd, 1H, J = 4.9, 11.2,
41.1 (Me), 58.2 (CH2), 63.2 (NCH), 127.1, 128.7, 377
1600, 1452, 1313,
1032, 820, 731
CH2), 3.77 (dd, 1 H, J = 5.2,11.2, CH2), 4.93 (dd, 129.4, 130.7, 132.2, 133.0, 134.3 (Ph, 4-ClC6H4),
1 H, J = 4.9, 5.2, NCH), 7.13–7.74 (m, 9 Harom), 150.2 (PhC), 159.8 (NC=N)
8.64 (br s, 1 H, NH)
3a
3b
3c
3d
4a
4b
4c
4d
5a
5b
5c
5d
3060, 2959, 1604,
1449, 1312, 741
4.13 (dd, 1 H, J = 5.3, 11.5, 5-H), 4.20 (dd, 1 H, 59.4 (CH2), 61.3 (NCH), 127.2, 127.9, 128.6,
J = 5.8, 11.5, 5-H), 5.21 (dd, 1 H, J = 5.3, 5.8, 6- 129.5, 131.3, 132.4, 133.1, 133.7 (2 × Ph),
263
297
279
313
309
343
325
359
295
329
311
345
H), 7.34–7.65 (m, 10 Harom
)
161.2 (PhC), 163.9 (NC=N)
3066, 2955, 1605,
1453, 1315, 826,
748
4.15 (dd, 1 H, J = 5.5, 11.8, 5-H), 4.23 (dd, 1 H, 59.6 (CH2), 61.7 (NCH), 127.2, 128.5, 129.4,
J = 5.9, 11.8, 5-H), 5.24 (dd, 1 H, J = 5.5, 5.9, 6- 130.6, 132.3, 133.2, 133.7, 134.6 (Ph, 4-
H), 7.34–7.74 (m, 9 Harom
)
ClC6H4), 161.2 (PhC), 164.0 (NC=N)
3062, 2958, 1598,
1454, 1317, 739
4.11 (dd, 1 H, J = 5.2, 11.3, 5-H), 4.19 (dd, 1 H, 59.2 (CH2), 61.2 (NCH), 127.0, 127.7, 128.6,
J = 5.7, 11.3, 5-H), 5.20 (dd, 1 H, J = 5.2, 5.7, 6- 129.3, 131.5, 132.2, 133.0, 133.8 (2 × Ph),
H), 7.31–7.60 (m, 10 Harom
)
150.0 (PhC), 159.4 (NC=N)
3065, 2955, 1603,
1450, 1319, 820,
742
4.12 (dd, 1 H, J = 5.3, 11.7, 5-H), 4.18 (dd, 1 H, 59.5 (CH2), 63.4 (NCH), 127.1, 128.3, 129.5,
J = 5.8, 11.7, 5-H), 5.22 (dd, 1 H, J = 5.3, 5.8, 6- 130.5, 132.1, 133.0, 133.6, 134.3 (Ph, 4-
H), 7.32–7.71 (m, 9 Harom
)
ClC6H4), 150.1 (PhC), 159.6 (NC=N)
3058, 2958, 1602,
1450, 1315, 738
2.19 (s, 3 H, Me), 4.80 (d, 1 H, J = 5.4, 5-H),
5.28 (d, 1 H, J = 5.4, 6-H), 7.30–7.64 (m, 10
18.2 (Me), 62.0 (NCH), 63.3 (SCH), 127.0,
127.7, 128.6, 129.5, 131.1, 132.3, 133.0, 133.9
(2 × Ph), 161.3 (PhC), 164.0 (C=N)
Harom
)
3068, 2952, 1600,
1455, 1318, 822,
735
2.19 (s, 3 H, Me), 4.81 (d, 1 H, J = 5.6, 5-H),
5.30 (d, 1 H, J = 5.6, 6-H), 7.35–7.76 (m, 9
18.3 (Me), 62.3 (NCH), 63.4 (SCH), 127.3,
128.5, 129.5, 130.7, 132.2, 133.0, 133.6, 134.4
(Ph, 4-ClC6H4), 161.3 (PhC), 164.2 (NC=N)
Harom
)
3060, 2959, 1597,
1450, 1315, 740
2.18 (s, 3 H, Me), 4.78 (d, 1 H, J = 5.2, 5-H),
5.26 (d, 1 H, J = 5.2, 6-H), 7.30–7.63 (m, 10
Harom)
18.1 (Me), 62.0 (NCH), 63.2 (SCH), 127.1,
127.7, 128.6, 129.4, 131.3, 132.1, 133.2, 133.9
(2 × Ph), 150.1 (PhC), 159.6 (NC=N)
3065, 2962, 1603,
1448, 1323, 823,
738
2.19 (s, 3 H, Me), 4.79 (d, 1 H, J = 5.3, 5-H),
5.28 (d, 1 H, J = 5.3, 6-H), 7.33–7.74 (m, 9
18.2 (Me), 62.2 (NCH), 63.3 (SCH), 127.2,
128.5, 129.3, 130.6, 132.2, 133.2, 133.9, 134.2
(Ph, 4-ClC6H4), 150.2 (PhC), 159.8 (NC=N)
Harom
)
3063, 2955, 1596,
1447, 1320, 740
2.60 (dd, 1 H, J = 4.9, 11.1, 6-H), 2.66 (dd, 1 H, 30.2 (CH2), 64.7 (NCH), 127.1, 127.6, 128.4,
J = 5.4, 11.1, 6-H), 5.19 (dd, 1 H, J = 4.9, 5.4, 7- 129.7, 131.0, 132.1, 132.8, 133.7 (2 × Ph),
H), 7.30–7.62 (m, 10 Harom
)
161.2, (PhC), 164.1 (NC=N)
3069, 2957, 1602,
1450, 1318, 825,
745
2.62 (dd, 1 H, J = 5.1, 11.3, 6-H), 2.69 (dd, 1 H, 30.3 (CH2), 64.8 (NCH), 127.4, 128.3, 129.4,
J = 5.7, 11.3, 6-H), 5.22 (dd, 1 H, J = 5.1, 5.7, 7- 130.3, 132.0, 133.2, 133.8, 134.6 (Ph, 4-
H), 7.31–7.66 (m, 9 Harom
)
ClC6H4), 161.4 (PhC), 164.3 (NC=N)
3065, 2956, 1598,
1455, 1322, 742
2.57 (dd, 1 H, J = 4.8, 11.0, 6-H), 2.63 (dd, 1 H, 30.1 (CH2), 64.5 (NCH), 127.4, 128.3, 129.5,
J = 5.3, 11.0, 6-H), 5.17 (dd, 1 H, J = 4.8, 5.3, 7- 130.6, 132.0, 132.9, 133.5 (2 × Ph), 150.0
H), 7.30–7.60 (m, 10 Harom
)
(PhC), 159.7 (NC=N)
3067, 2962, 1601,
1458, 1320, 820,
743
2.60 (dd, 1 H, J = 5.0, 11.2, 6-H), 2.66 (dd, 1 H, 30.2 (CH2), 64.7 (NCH), 127.3, 128.4, 129.3,
J = 5.6, 11.2, 6-H), 5.17 (dd, 1 H, J = 5.0, 5.6, 7- 130.1, 130.9, 132.5, 133.6, 134.4 (Ph, 4-
H), 7.30–7.65 (m, 9 Harom
)
ClC6H4), 150.1 (PhC), 159.9 (NC=N)
a IR (KBr): 1030–1035 (S=O) cm–1, this IR band was absent in case of compounds 3–5.
(2) Arranz, M. E.; Diaz, J. A.; Ingate, S. T.; Witvrouw, M.;
Pannecouque, C.; Balzarini, J.; Clercq, E. D.; Vega, S. J.
Med. Chem. 1998, 41, 4109.
(3) Neilla, C. G.; Prestona, P. N.; Wightmana, R. H.
Tetrahedron 1998, 54, 13645.
Acknowledgment
We sincerely thank RSIC, Lucknow, India, for providing microana-
lyses and spectra.
(4) Badger, A. M.; Bradbeer, J. N.; Votta, B.; Lee, J. C.; Adams,
J. L.; Griswold, D. E. J. Pharmacol. Exp. Ther. 1996, 279,
1453.
(5) Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.;
Pridgen, L. N. J. Org. Chem. 1997, 62, 8449.
References
(1) Arranz, M. E.; Diaz, J. A.; Ingate, S. T.; Witvrouw, M.;
Pannecouque, C.; Balzarini, J.; Clercq, E. D.; Vega, S.
Bioorg. Med.Chem. 1999, 7, 2811.
Synthesis 2003, No. 7, 1079–1082 ISSN 0039-7881 © Thieme Stuttgart · New York