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HRMS (ESI): m/z calcd for C9H10N3ClSeNa: 297.9618; found:
6-tert-Butyl-4-(1-pyrrolidinyl)selenolo[3,2-d][1,2,3]triazine (1a)
297.9633.
Yield: 88%; pale-orange solid; mp 182 °C.
1H NMR (250 MHz, DMSO-d6): d = 1.42 (s, 9 H, 3 × CH3), 1.99
4-Chloro-6-phenylselenolo[3,2-d][1,2,3]triazine (2)
Yield: 85%; brown solid; mp 135 °C.
1H NMR (250 MHz, DMSO-d6): d = 7.57 (m, 3 H, 3 × CH), 8.01
(m, 2 H, 2 × CH), 8.73 (s, 1 H, CH).
13C NMR (62.9 MHz, DMSO-d6): d = 121.6, 127.6, 129.6, 131.4,
132.9, 133.6, 154.7, 160.9, 161.6.
(m, 4 H, 2 × CH2), 3.81 (m, 4 H, 2 × CH2), 7.60 (s, 1 H, CH).
13C NMR (62.9 MHz, DMSO-d6): d = 24.7, 32.1, 36.8, 47.1, 115.0,
120.9, 152.9, 157.5, 172.9.
HRMS (ESI): m/z calcd for C13H19N4Se: 311.0770; found:
311.0765.
HRMS (ESI): m/z calcd for C11H7N3ClSe: 295.9488; found:
6-Phenyl-4-(1-pyrrolidinyl)selenolo[3,2-d][1,2,3]triazine (2a)
295.9486.
Yield: 98%; brown solid; mp 232 °C.
1H NMR (250 MHz, DMSO-d6): d = 2.03 (m, 4 H, 2 × CH2), 3.84
(m, 4 H, 2 × CH2), 7.49 (m, 3 H, 3 × CH), 7.85 (m, 2 H, 2 × CH),
8.27 (s, 1 H, CH).
13C NMR (62.9 MHz, DMSO-d6): d = 24.7, 47.2, 115.8, 122.0,
126.8, 129.4, 130.1, 133.5, 152.8, 156.1, 158.0.
4-Chloro-6-(4-methylphenyl)selenolo[3,2-d][1,2,3]triazine (3)
Yield: 94%; orange solid; mp 154 °C.
1H NMR (250 MHz, pyridine-d5): d = 2.23 (s, 3 H, CH3), 7.25 (d,
J = 7.8 Hz, 2 H, 2 × CH), 7.74 (d, J = 7.8 Hz, 2 H, 2 × CH), 8.45 (s,
1 H, CH).
13C NMR (62.9 MHz, pyridine-d5): d = 21.7, 121.8, 128.3, 131.0,
131.5, 134.2, 142.6, 155.8, 162.2, 162.7.
HRMS (ESI): m/z calcd for C15H15N4Se: 331.0457; found:
331.0477.
HRMS (ESI): m/z calcd for C12H9N3ClSe: 309.9645; found:
309.9613.
6-(4-Methylphenyl)-4-(1-pyrrolidinyl)selenolo[3,2-d][1,2,3]tri-
azine (3a)
Yield: 96%; dark-red solid; mp 235 °C.
4-Chloro-6-(4-methoxyphenyl)selenolo[3,2-d][1,2,3]triazine (4)
Yield: 85%; brown solid; mp 145 °C.
1H NMR (250 MHz, DMSO-d6): d = 3.85 (s, 3 H, OCH3), 7.10 (d,
J = 8.7 Hz, 2 H, 2 × CH), 7.97 (d, J = 8.7 Hz, 2 H, 2 × CH), 8.57 (s,
1 H, CH).
13C NMR (62.9 MHz, DMSO-d6): d = 55.6, 114.9, 119.6, 125.5,
129.4, 132.9, 154.3, 161.3, 161.6, 161.8.
1H NMR (250 MHz, DMSO-d6): d = 2.02 (m, 4 H, 2 × CH2), 2.35
(s, 3 H, CH3), 3.84 (m, 4 H, 2 × CH2), 7.31 (d, J = 8 Hz, 2 H,
2 × CH), 7.75 (d, J = 8 Hz, 2 H, 2 × CH), 8.20 (s, 1 H, CH).
13C NMR (62.9 MHz, DMSO-d6): d = 20.8, 24.7, 47.2, 115.4, 121.1,
126.7, 130.0, 130.8, 140.1, 152.8, 156.3, 158.1.
HRMS (ESI): m/z calcd for C16H17N4Se: 345.0613; found:
345.0590.
HRMS (ESI): m/z calcd for C12H9ON3ClSe: 325.9594; found:
325.9679.
6-(4-Methoxyphenyl)-4-(1-pyrrolidinyl)selenolo[3,2-
d][1,2,3]triazine (4a)
4-Chloro-6-(4-chlorophenyl)selenolo[3,2-d][1,2,3]triazine (5)
Yield: 93%; brown solid; mp 195 °C.
Yield: 95%; pale-brown solid; mp 164 °C.
1H NMR (250 MHz, pyridine-d5): d = 1.74 (m, 4 H, 2 × CH2), 3.66
(m, 4 H, 2 × CH2), 3.71 (s, 3 H, OCH3), 7.07 (d, J = 8.7 Hz, 2 H,
2 × CH), 7.78 (d, J = 8.7 Hz, 2 H, 2 × CH), 8.27 (s, 1 H, CH).
1H NMR (250 MHz, DMSO-d6): d = 7.63 (d, J = 8.6 Hz, 2 H,
2 × CH), 8.04 (d, J = 8.6 Hz, 2 H, 2 × CH), 8.74 (s, 1 H, CH).
13C NMR (62.9 MHz, DMSO-d6): d = 122.4, 129.4, 129.5, 131.8,
133.8, 136.1, 154.7, 159.9, 160.8.
13C NMR (62.9 MHz, pyridine-d5): d = 25.7, 48.0, 55.9, 115.6,
116.7, 121.8, 127.7, 129.3, 154.0, 157.1, 159.9, 162.1.
HRMS (ESI): m/z calcd for C11H6N3Cl2Se: 329.9099; found:
HRMS (ESI): m/z calcd for C16H17ON4Se: 361.0562; found:
329.9099.
361.0568.
10-Chloro-5,6-dihydronaphtho[2¢,1¢:4,5]selenolo[3,2-
d][1,2,3]triazine (6)
Yield: 92%; pale-brown solid; mp 149 °C.
6-(4-Chlorophenyl)-4-(1-pyrrolidinyl)selenolo[3,2-d][1,2,3]tri-
azine (5a)
Yield: 91%; pale-brown solid; mp 270 °C.
1H NMR (250 MHz, DMSO-d6): d = 3.09 (m, 2 H, CH2), 3.20 (m,
2 H, CH2), 7.37 (m, 3 H, 3 × CH), 7.66 (m, 1 H, CH).
13C NMR (62.9 MHz, DMSO-d6): d = 22.0, 26.9, 126.9, 127.6,
128.6, 130.1, 131.2, 132.8, 133.3, 137.3, 152.5, 154.7, 158.4.
1H NMR (250 MHz, pyridine-d5): d = 1.75 (m, 4 H, 2 × CH2), 3.71
(m, 4 H, 2 × CH2), 7.49 (d, J = 8.7 Hz, 2 H, 2 × CH), 7.74 (d,
J = 8.7 Hz, 2 H, 2 × CH), 8.36 (s, 1 H, CH).
13C NMR (62.9 MHz, pyridine-d5): d = 26.8, 49.2, 118.8, 124.3,
130.4, 130.7, 131.4, 135.0, 155.1, 156.6, 160.6.
HRMS (ESI): m/z calcd for C13H9N3ClSe: 321.9645; found:
321.9599.
HRMS (ESI): m/z calcd for C15H14N4ClSe: 365.0067; found:
365.0047.
Synthesis of Aminoselenolotriazine Derivatives 1a–6b; General
Procedure
10-(1-Pyrrolidinyl)-5,6-dihydronaphtho[2¢,1¢:4,5]selenolo[3,2-
d][1,2,3]triazine (6a)
Yield: 94%; pale-brown solid; mp 299 °C.
1H NMR (250 MHz, pyridine-d5): d = 1.74 (m, 4 H, 2 × CH2), 2.88
(m, 2 H, CH2), 3.22 (m, 2 H, CH2), 3.74 (m, 4 H, 2 × CH), 7.23 (m,
3 H, 3 × CH), 7.46 (m, 1 H, CH).
The appropriate chloroselenolotriazine (1 mmol) and corresponding
amine (10 mL) were heated under microwave irradiation (P = 100
W, t = 15 min, Tmax = 150 °C). The mixture was cooled to r.t. and
poured into H2O (80 mL) under stirring. The precipitate formed was
filtered, washed several times with H2O and dried at r.t. overnight.
The products were recrystallized from MeCN (2 mL) to give prod-
ucts 1a–6b.
13C NMR (62.9 MHz, pyridine-d5): d = 23.3, 25.7, 28.6, 47.9, 116.8,
126.5, 128.2, 129.3, 130.4, 132.3, 134.8, 137.6, 148.1, 154.3, 156.9.
Synthesis 2009, No. 20, 3472–3476 © Thieme Stuttgart · New York