H
J. O. Strelnikova et al.
Paper
Synthesis
IR (KBr): 3075, 2990, 1760, 1635, 1560, 1490, 1450 cm–1
.
HRMS (ESI-TOF): m/z [M + Na]+ calcd for C20H17F3N2O4Na: 429.1033;
found: 429.1044.
1H NMR (400 MHz, CDCl3): = 8.40–8.37 (m, 1 H), 8.35–8.28 (m, 3 H),
7.70 (t, J = 7.4 Hz, 1 H), 7.60–7.53 (m, 3 H), 7.44 (t, J = 7.9 Hz, 1 H),
4.46–4.30 (m, 2 H), 1.34 (t, J = 7.1 Hz, 3 H).
Ethyl 4-Benzyl-6-phenyl-2-(trifluoromethyl)-2H-1,3,5-oxadiazine-
2-carboxylate (3m)
13C NMR (100 MHz, CDCl3): = 163.8, 163.2, 159.1, 136.0, 134.54,
134.48, 132.4, 129.6, 129.4, 129.3, 128.8, 128.7, 126.9, 120.8 (q, 1JC,F
285.1 Hz), 90.1 (q, 2JC,F = 32.6 Hz), 63.6, 13.9.
=
Compound 3m was prepared from oxadiazole 1i (47.2 mg, 0.2 mmol)
and diazo compound 2h (91 mg, 0.5 mmol) according to the general
procedure; yield: 73 mg (94%); colorless oil.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C19H1535ClF3N2O3: 411.0718;
found: 411.0700.
IR (KBr): 3065, 3035, 2985, 1745, 1655, 1605, 1575, 1495, 1450, 1395,
1370 cm–1
.
1H NMR (400 MHz, CDCl3): = 8.15–8.11 (m, 2 H), 7.63 (t, J = 7.4 Hz,
1 H), 7.48 (t, J = 7.8 Hz, 2 H), 7.45–7.40 (m, 2 H), 7.35 (t, J = 7.4 Hz,
2 H), 7.31–7.25 (m, 1 H), 4.43–4.28 (m, 2 H), 3.84 (s, 2 H), 1.31 (t, J =
7.1 Hz, 3 H).
13C NMR (100 MHz, CDCl3): = 165.8, 163.2, 163.1, 135.4, 134.2,
129.3, 129.2, 129.1, 128.6, 128.5, 126.9, 120.6 (q, 1JC,F = 285.0 Hz), 89.3
(q, 2JC,F = 32.2 Hz), 63.5, 44.6, 13.8.
Ethyl 4-(2-Methylphenyl)-6-phenyl-2-(trifluoromethyl)-2H-1,3,5-
oxadiazine-2-carboxylate (3j)
Compound 3j was prepared from oxadiazole 1f (47.2 mg, 0.2 mmol)
and diazo compound 2h (91 mg, 0.5 mmol) according to the general
procedure; yield: 75 mg (96%); white solid; mp 60–62 °C.
IR (KBr): 3070, 2990, 1750, 1635, 1570, 1455, 1350 cm–1
.
1H NMR (400 MHz, CDCl3): = 8.31–8.29 (m, 2 H), 8.13 (dd, J = 7.7, 1.2
Hz, 1 H), 7.71–7.65 (m, 1 H), 7.55 (t, J = 7.7 Hz, 2 H), 7.42 (t, J = 7.4, 1.4
Hz, 1 H), 7.36–7.29 (m, 2 H), 4.46–4.32 (m, 2 H), 2.69 (s, 3 H), 1.34 (t,
J = 7.1 Hz, 3 H).
HRMS (ESI-TOF): m/z [M + H]+ calcd for C20H18F3N2O3: 391.1264;
found: 391.1279.
Ethyl 6-(4-Methoxyphenyl)-4-phenyl-2-(trifluoromethyl)-2H-
1,3,5-oxadiazine-2-carboxylate (3n)
13C NMR (100 MHz, CDCl3): = 163.4, 162.8, 162.2, 139.2, 134.2,
2
133.9, 131.7, 131.0, 130.3, 129.6, 129.2, 128.7, 125.7, 120.8 (q, JC,F
=
285.0 Hz), 89.7 (q, 2JC,F = 32.6 Hz), 63.5, 22.0, 13.9.
Compound 3n was prepared from oxadiazole 1j (50.4 mg, 0.2 mmol)
and diazo compound 2h (91 mg, 0.5 mmol) according to the general
procedure; yield: 76 mg (94%); white solid; mp 64−66 °C.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C20H18F3N2O3: 391.1264;
found: 391.1263.
IR (KBr): 2975, 2840, 1755, 1625, 1550, 1510, 1425, 1360 cm–1
.
1H NMR (400 MHz, CDCl3): = 8.43–8.38 (m, 2 H), 8.32–8.27 (m, 2 H),
7.60–7.54 (m, 1 H), 7.50 (t, J = 7.4 Hz, 2 H), 7.04 (d, J = 9.0 Hz, 2 H),
4.44–4.29 (m, 2 H), 3.93 (s, 3 H), 1.32 (t, J = 7.1 Hz, 3 H).
13C NMR (100 MHz, CDCl3): = 164.7, 163.7, 163.1, 160.2, 134.4,
132.2, 131.5, 128.7, 128.2, 121.7, 120.9 (q, 1JC,F = 285.0 Hz), 114.1, 90.1
(q, 2JC,F = 32.3 Hz), 63.4, 55.6, 13.9.
Ethyl 4-(Naphthalen-2-yl)-6-phenyl-2-(trifluoromethyl)-2H-1,3,5-
oxadiazine-2-carboxylate (3k)
Compound 3k was prepared from oxadiazole 1g (54.4 mg, 0.2 mmol)
and diazo compound 2h (91 mg, 0.5 mmol) according to the general
procedure; yield: 83 mg (97%); white solid; mp 93–95 °C.
IR (KBr): 3065, 2995, 1755, 1620, 1555, 1490, 1450, 1365 cm–1
.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C20H18F3N2O4: 407.1213;
found: 407.1193.
1H NMR (400 MHz, CDCl3): = 9.0 (s, 1 H), 8.43 (dd, J = 8.7, 1.6 Hz,
1 H), 8.42–8.37 (m, 2 H), 8.06 (d, J = 7.6 Hz, 1 H), 7.93 (t, J = 8.1 Hz, 2
H), 7.72 (t, J = 7.4 Hz, 1 H), 7.64–7.55 (m, 4 H), 4.47–4.32 (m, 2 H), 1.34
(t, J = 7.1 Hz, 3 H).
Ethyl 6-(4-Nitrophenyl)-4-phenyl-2-(trifluoromethyl)-2H-1,3,5-
oxadiazine-2-carboxylate (3o)
13C NMR (100 MHz, CDCl3): = 163.5, 163.3, 159.9, 135.5, 134.2,
Compound 3o was prepared from oxadiazole 1k (53.4 mg, 0.2 mmol)
and diazo compound 2h (91 mg, 0.5 mmol) according to the general
procedure; yield: 60 mg (71%); pale yellow solid; mp 114–116 °C.
132.7, 131.5, 130.3, 129.7, 129.5, 129.3, 128.7, 128.1, 127.9, 127.8,
126.4, 124.7, 120.9 (q, JC,F = 285.3 Hz), 90.2 (q, JC,F = 32.0 Hz), 63.5,
13.9.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C23H18F3N2O3: 427.1264;
1
2
IR (KBr): 3110, 3005, 1750, 1635, 1530, 1425, 1355 cm–1
.
1H NMR (400 MHz, CDCl3): = 8.52−8.47 (m, 2 H), 8.43–8.37 (m, 4 H),
7.61 (t, J = 7.3 Hz, 1 H), 7.53 (t, J = 7.6 Hz, 2 H), 4.47–4.31 (m, 2 H), 1.36
(t, J = 7.1 Hz, 3 H).
found: 427.1248.
Ethyl 4-(Phenoxymethyl)-6-phenyl-2-(trifluoromethyl)-2H-1,3,5-
13C NMR (100 MHz, CDCl3): = 163.1, 161.5, 159.3, 151.2, 135.3,
133.5, 132.9, 130.2, 128.9, 128.5, 123.7, 120.6 (q, 1JC,F = 285.1 Hz), 90.5
(q, 2JC,F = 32.8 Hz), 63.8, 13.9.
oxadiazine-2-carboxylate (3l)
Compound 3l was prepared from oxadiazole 1h (50.4 mg, 0.2 mmol)
and diazo compound 2h (91 mg, 0.5 mmol) according to the general
procedure; yield: 77 mg (95%); colorless oil.
HRMS (ESI-TOF): m/z [M + H]+ calcd for C19H15F3N3O5: 422.0958;
IR (KBr): 3065, 2930, 1755, 1665, 1600, 1550, 1535, 1495, 1450, 1395
found: 422.0956.
cm–1
.
1H NMR (400 MHz, CDCl3): = 8.21–8.16 (m, 2 H), 7.67 (t, J = 7.4 Hz,
1 H), 7.52 (t, J = 7.8 Hz, 2 H), 7.34–7.28 (m, 2 H), 7.05–6.97 (m, 3 H),
4.89 (s, 2 H), 4.41–4.25 (m, 2 H), 1.29 (t, J = 7.1 Hz, 3 H).
Ethyl 6-(4-Chlorobenzyl)-4-phenyl-2-(trifluoromethyl)-2H-1,3,5-
oxadiazine-2-carboxylate (3p)
Compound 3p was prepared from oxadiazole 1l (51.3 mg, 0.2 mmol)
and diazo compound 2h (91 mg, 0.5 mmol) according to the general
procedure; yield: 80 mg (94%); colorless oil.
IR (KBr): 3070, 2985, 2930, 1750, 1685, 1530, 1490, 1450, 1375 cm–1
13C NMR (100 MHz, CDCl3): = 164.0, 163.3, 162.8, 158.3, 134.6,
1
129.42, 129.37, 128.8, 128.7, 121.5, 120.5 (q, JC,F = 285.3 Hz), 115.2,
89.5 (q, 2JC,F = 32.9 Hz), 69.4, 63.7, 13.8.
.
© 2020. Thieme. All rights reserved. Synthesis 2020, 52, A–K