834
C.-W. Sun, H.-F. Wang, J. Zhu, D.-R. Yang, J. Jin, and J.-H. Xing
Vol 48
381.1; Anal. Calcd. for C15H17ClN6O2S: C, 47.30; H, 4.50; N,
22.07.; Found C, 47.47; H, 4.43; N, 22.10.
(d, 1H, J ¼ 4.4 Hz, pyri-H), 9.59 (s, 1H, NAH) ppm;
[MþH]þ: 368.1; Anal. Calcd. for C13H14ClN7O2S: C, 42.45;
H, 3.84; N, 26.66.; Found C, 42.49; H, 3.87; N, 24.61.
1-((6-Chloropyridin-3-yl)methyl)-5-((5-chlorothiazol-3-yl)
methyl)-1,3,5-hexahydrotriazine-2-(N-nitro) imine(7u). Yield:
63.6%; m.p.: 168–170ꢀC; IR (KBr disc): 3278, 1634, 1590,
1152, 1102 cmꢁ1 1H-NMR (DMSO-d6), 4.30 (s, 2H, tria-
;
zine),4.42 (t, J ¼ 0.8 Hz 2H, triazine), 4.57 (s, 2H, CH2-Pyri),
4.61 (s, 2H, CH2-thiazole), 7.36 (s,1H, thiazole-H), 7.45 (d, J ¼
3.6 Hz, 1H, Pyri-H), 7.75–7.77 (dd, J1 ¼ 2.4 Hz, J2 ¼ 2.8, 1H,
Pyri-H), 8.30 (d, J ¼ 2.4 Hz, 1H, Pyri-H), 9.52 (s, 1H, NAH)
ppm; [MþH]þ: 403.1; Anal. Calcd. for C13H13Cl2N7O2S: C,
38.82; H, 3.26; N, 24.37.; Found C, 38.71; H, 3.35; N, 24.22.
1-((2-Chlorothiazol-5-yl)methyl)-5-((2-chlorothiazol-5-yl)
methyl)-1,3,5-hexahydrotriazine-2-(N-nitro) imine (7v). Yield:
57.9%; m.p.: 153–155ꢀC; IR (KBr disc): 3283, 1655, 1593,
(R)-1-((6-Chloropyridin-3-yl)methyl)-5-(1-phenylethyl)-1,3,5-
hexahydrotriazine-2-(N-nitro) imine (7o). Yield: 57.6%; m.p.:
165ꢃ166ꢀC; IR (KBr disc): 3289, 1587, 1534, 1152, 1100
cmꢁ1 1H-NMR (DMSO-d6), 1.39–1.41 (m, 3H, CH3), 3.64
;
(dd, J1 ¼ J2 ¼ 6.4 Hz, CH2APh), 4.31 (s, 2H, triazine), 4.42
(s, 2H, triazine), 4.57 (s, 2H, CH2-thiazole), 7.24–7.35 (m, 5H,
PhAH), 7.37 (d, J ¼ 8.0 Hz, 1H, Pyri-H), 7.82–7.85 (m, 1H,
Pyri-H), 8.33 (d, J ¼ 2.4 Hz, 1H, Pyri-H), 9.61 (s, 1H, NAH)
ppm; [MþH]þ: 375.7; Anal. Calcd. for C17H19ClN6O2: C,
54.47; H, 5.11; N, 22.42; Found C, 54.33; H, 5.18; N, 22.48;
25
[|A]D ¼ þ23.38ꢀ (C ¼ 0.01 g/mL, CH3CH2OH).
´
(R)-1-((2-Chlorothiazol-5-yl)methyl)-5-(1-phenylethyl)-1,3,5-
hexahydro-triazine-2-(N-nitro) imine(7p). Yield: 62.3%; m.p.:
145ꢃ146ꢀC; IR (KBr disc): 3291, 1584, 1541, 1148, 1105
cmꢁ1
;
1H-NMR (DMSO-d6), 1.42–1.44 (m, 3H, CH3), 3.63
1158, 1107 cmꢁ1
;
1H-NMR (DMSO-d6), 4.22 (d, J ¼ 3.2 Hz
(dd, J1 ¼ J2 ¼ 6.4 Hz, CH2APh), 4.34 (s, 2H, triazine), 4.42
(s, 2H, triazine), 4.56 (s, 2H, CH2-thiazole), 7.28–7.36 (m, 5H,
PhAH), 7.38 (d, J ¼ 8.0 Hz, 1H, Pyri-H), 7.81–7.83 (m, 1H,
Pyri-H), 8.34 (d, J ¼ 2.4 Hz, 1H, Pyri-H), 9.63 (s, 1H, NAH)
ppm; [MþH]þ: 381.1; Anal. Calcd. for C15H17ClN6O2S: C,
2H, triazine), 4.60 (d, J ¼ 1.2 Hz 2H, triazine), 4.55 (s, 2H,
CH2-thiazole), 4.62 (s, 2H, CH2-thiazole), 7.38 (s, 1H, thia-
zole-H), 7.42 (s, 1H, thiazole-H), 9.45 (s, 1H, NAH) ppm;
[MþH]þ: 409.3; Anal. Calcd. for C11H11Cl2N7O2S2: C, 32.36;
H, 2.72; N, 24.01.; Found C, 32.28; H, 2.83; N, 24.17.
47.30; H, 4.50; N, 22.07.; Found C, 47.37; H, 4.38; N, 22.11;
1-((6-Chloropyridin-3-yl)methyl)-5-(2-furfuryl)-1,3,5-hexa-
hydrotriazine-2-(N-nitro) imine (7w). Yield: 54.3%; m.p.:
147–149ꢀC; IR (KBr disc): 3289, 1587, 1543, 1165, 1103
25
[|A]D ¼ þ27.44ꢀ (C ¼ 0.01 g/mL, CH3CH2OH).
´
1-((6-Chloropyridin-3-yl)methyl)-5-phenethyl-1,3,5-hexahy-
drotriazine-2-(N-nitro) imine (7q). Yield: 54.3%; m.p.: 147–
1
cmꢁ1; H-NMR (DMSO-d6), 3.61 (s, 2H, CH2-furan), 4.30 (s,
1
149ꢀC; IR (KBr disc): 3311, 1590, 1553, 1125, 1104 cmꢁ1; H-
2H, triazine),4.43 (s, 2H, triazine), 4.63 (s, 2H, CH2-Pyri),
6.22 (d, J ¼ 3.2 Hz, 1H, furan-H), 6.33–6.35 (m, 1H, furan-
H), 7.40–7.41 (dd, J1 ¼ J2 ¼ 0.8 Hz, 1H, furan-H), 7.36 (d, J
¼ 8.0 Hz, 1H, Pyri-H), 7.81–7.84 (m, 1H, Pyri-H), 8.25 (d, J
¼ 2.4 Hz, 1H, Pyri-H), 9.68 (s, 1H, NAH) ppm; [MþH]þ:
351.9; Anal. Calcd. for C14H15ClN6O3: C, 47.94; H, 4.31; N,
23.96.; Found C, 47.82; H, 4.37; N, 23.84.
NMR (DMSO-d6), 2.66–2.71 (m, 2H, CH2APh), 2.73–2.90 (m,
N-2H-Bz, 4.24 (s, 2H, triazine), 4.44 (s, 2H, triazine), 4.57 (s, 2H,
CH2-Pyri), 7.05 (d, J ¼ 7.2 Hz, 1H, PhAH), 7.22–7.36 (m, 1H,
PhAH), 7.83 (d, J ¼ 8.0 Hz, 1H, Pyri-H), 8.27–8.31 (dd, J1 ¼ J2
¼ 2.4 Hz, Pyri-H), 8.74 (d, J ¼ 2.4 Hz, 1H, Pyri-H), 9.65 (s, 1H,
NAH) ppm; [MþH]þ: 375.8; Anal. Calcd. for C17H19ClN6O2: C,
54.47; H, 5.11; N, 22.42.; Found C, 54.32; H, 5.29; N, 22.37.
1-((2-Chlorothiazol-5-yl)methyl)-5-phenethyl-1,3,5-hexahy-
drotriazine-2-(N-nitro) imine (7r). Yield: 57.1%; m.p.: 159–
1-((2-Chlorothiazol-5-yl)methyl)-5-(2-furfuryl)-1,3,5-hexa-
hydrotriazine-2-(N-nitro) imine (7x). Yield: 62.5%; m.p.:
154–155ꢀC; IR (KBr disc): 3289, 1592, 1548, 1165, 1101
1
1
160ꢀC; IR (KBr disc): 3260, 1586, 1531, 1152, 1107 cm-1; H-
cmꢁ1; H-NMR (DMSO-d6), 3.74 (s, 2H, CH2-furan), 4.36 (s,
NMR (DMSO-d6), 2.74–2.75 (m,2H, CH2APh), 2.75–2.76 (m,
N-2H-Bz), 4.58 (m, 2H, CH2-thiazole), 4.38 (s, 2H, triazine),
4.41 (s, 2H, triazine),7.06–7.11 (d, 1H, PhAH,), 7.20–7.35 (m,
4H, PhAH), 7.43 (s,1H, thiazole-H), 9.52 (s, 1H, NAH) ppm;
[MþH]þ: 381.1; Anal. Calcd. for C15H17ClN6O2S: C, 47.30; H,
4.50; N, 22.07.; Found C, 47.17; H, 4.58; N, 22.04.
2H, triazine),4.45 (d, J ¼ 0.8 Hz, 2H, triazine), 4.62 (s, 2H,
thiazole-CH2), 6.07 (d, J ¼ 2.8 Hz, 1H, furan-H), 6.34–6.35
(m, 1H, furan-H), 7.40–7.41 (dd, J1 ¼ J2 ¼ 1.2 Hz, 1H, furan-
H), 7.43 (1H,s,thiazole-H), 9.55 (s, 1H, NAH) ppm; [MþH]þ:
357.1; Anal. Calcd. for C12H13ClN6O3S: C 40.40, H 3.67, N
23.55; found C 40.39, H 3.72, N 23.52.
1-((6-Chloropyridin-3-yl)methyl)-5-(3-pyridylmethyl)-1,3,5-
hexahydrotriazine-2-(N-nitro) imine (7s). Yield: 51.7%; m.p.:
132–134ꢀC; IR (KBr disc): 3288, 1593, 1338, 1175, 1103
(6)-1-((6-Chloropyridin-3-yl)methyl)-5-(2-tetrahydrofurfuryl)-
1,3,5-hexahydrotriazine-2-(N-nitro) imine (7y). Yield: 59.4%;
m.p.: 134–135ꢀC; IR (KBr disc): 3260, 1586, 1531, 1152, 1107
1
1
cmꢁ1; H NMR (DMSO-d6), 3.89 (s, 2H, triazine), 4.35 (s, 2H,
cmꢁ1; H-NMR (DMSO-d6), 1.40–1.44 (m, 1H, H-THF), 1.80–
triazine), 4.50 (d, J ¼ 1.2 Hz, 2H, CH2-Pyri), 4.63 (d, 2H, CH2-
Pyri), 7.12 (d, J ¼ 7.6 Hz, 1H, Pyri-H), 7.23–7.27 (m, 1H, Pyri-
H), 7.36 (d, J ¼ 8.0 Hz, 1H, Pyri-H), 7.65–7.67 (m, 1H,
Pyri-H), 7.49 (d, J ¼ 8.0 Hz, 1H, Pyri-H), 8.13–8.15 (m, 1H,
Pyri-H), 8.69 (d, J ¼ 2.4 Hz, 1H, Pyri-H), 9.87 (s, 1H, NAH)
ppm; [MþH]þ: 362.1; Anal. Calcd. for C15H16ClN7O2: C,
49.80; H, 4.46; N, 27.10.; Found C, 49.93; H, 4.51; N, 27.22.
1-((2-Chlorothiazol-5-yl)methyl)-5-(3-pyridylmethyl)-1,3,5-
hexahydrotriazine-2-(N-nitro) imine (7t). Yield: 58.3%; m.p.:
188–189ꢀC; IR (KBr disc): 3445, 1537, 1399, 1107, 1047
1.88 (m, 3H, H-THF), 2.53–2.56 (m,2H, H-THF), 3.85–3.92 (m,
1H, H-THF), 4.36–4.40 (t, J ¼ 12.4 Hz, 2H, triazine), 4.48–4.54
(t, J ¼ 12.4 Hz, 2H, triazine), 4.61 (s, 2H, CH2-Pyri), 7.83 (d, J
¼ 8.0 Hz, 1H, Pyri-H), 8.27–8.31 (dd, J1 ¼ J2 ¼ 2.4 Hz, Pyri-
H), 8.74 (d, J ¼ 2.4 Hz, 1H, Pyri-H), 9.53 (s, 1H, NAH) ppm;
[MþH]þ: 356.1; Anal. Calcd. for C14H19ClN6O3: C 47.39, H
5.40, N 23.69; found C 47.28, H 5.37, N 23.52.
(6)-1-((2-Chlorothiazol-5-yl)methyl)-5-(2-tetrahydrofurfuryl)-
1,3,5-hexahydrotriazine-2-(N-nitro) imine(7z). Yield: 63.3%;
m.p.: 127–128ꢀC; IR (KBr disc): 3260, 1586, 1531, 1152,
1
cmꢁ1
;
1H-NMR (DMSO-d6), 3.89 (s, 2H, pyridine-CH2), 4.42
1107 cmꢁ1; H-NMR (DMSO-d6), 1.38–1.48 (m, 1H, H-THF),
(s, 2H, triazine-2H), 4.50 (s, 2H, triazine-H), 4.63 (s, 2H, CH2-
thiazole), 7.11–7.13 (d, J ¼ 8 Hz, 1H, pyri-H), 7.36 (s, 1H,
thiazole-H), 7.69–7.72 (d, 1H, J ¼ 8 Hz, pyri-H), 7.61–7.60
1.81–1.99 (m, 3H, H-THF), 2.55–2.66 (m,2H, H-THF), 3.94–
3.99 (m, 1H, H-THF), 4.38–4.43 (t, J ¼ 12.4 Hz, 2H, triazine),
4.53–4.61 (t, J ¼ 11.2 Hz, 2H, triazine), 4.63 (s, 2H, thiazole-
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet