AN EFFICIENT MULTICOMPONENT SYNTHESIS OF TETRAHYDROPYRANS
1007
−
1
−1
structure of the products was confirmed by comparison
(4f). IR (KBr, cm ): 3287, 2940, 2210, 1620 cm ;
1H NMR (400 MHz, DMSO-d ): 1.15 (s, 3H, CH ), 1.12
with their physical and spectral data with literature values
6
3
1
for authentic samples. The spectral data IR, H NMR,
(s, 3H, CH ), 3.17(s, 3H), 2.37 (s, 2H, CH ), 2.44 (m, 2H,
3
2
13
C NMR and MS of all synthesized tetrahydrobenzo-
CH ), 4.76 (s, 1H, CH), 5.83 (s, 2H, NH ), 7.47–7.91
2
2
pyran derivatives are reported below.
(m, 4H, ArH); MS (m/z) = 325 (M + 1).
2
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(4-
Spectral Data
hydroxyphenyl)-5-oxo-4H-chromene-3-carbonitrile
4g). IR (KBr, cm ): 3431, 2890, 2290, 1660 cm ;
H NMR (400 MHz, DMSO-d ): 1.07 (s, 3H, CH ), 1.09
−
1
−1
(
1
(
2
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-
phenyl)-5-oxo-4H-chromene-3-carbonitrile (4a). IR
KBr, cm ): 3382, 3327, 3170, 2954, 2192, 1681, 1656,
360 cm ; H NMR (400 MHz, DMSO-d ): 0.96 (s, 3H,
6
3
(
(
1
s, 3H, CH ), 8.9 (s, 1H), 2.89 (s, 2H, CH ), 2.78 (m, 2H,
3
2
−
1
CH ), 5.32 (s, 1H, CH), 5.54 (s, 2H, NH ), 7.65–7.87 (m,
2
2
−1 1
6
4H, ArH); MS (m/z) = 311 (M + 1).
CH ), 1.07 (s, 3H, CH ), 2.09 (d, J = 16.0 Hz, 1H), 2.23
3
3
2
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(3,4-
(
(
(
d, J =16.0Hz, 1H), 2.50 (m, 2H, CH ), 4.11 (s, 1H), 7.06
s, br, 2H, NH ), 7.19 (m, 3H, ArH), 7.33 (m, 2H); MS
2
dimethoxyphenyl)-5-oxo-4H-chromene-3-carbonitrile
4h). IR (KBr, cm ): 3190, 2278 cm ; 1H NMR
400 MHz, DMSO-d ): 1.01 (s, 3H, CH ), 1.12 (s, 3H,
2
−1
−1
(
(
m/z) = 294 (M + 1).
6
3
2
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(4-
CH ), 2.92 (s, 3H), 3.05 (s, 3H), 2.26 (s, 2H, CH ),
3
2
chlorophenyl)-5-oxo-4H-chromene-3-carbonitrile
2
.46–2.48 (m, 2H, CH ), 4.43 (s, 1H, CH), 6.58 (s, 2H,
2
−
1
(
4b). IR (KBr, cm ): 3303, 3041, 2994, 2246, 1653,
NH ), 7.18 (d, H, J = 2.2 Hz,ArH), 7.34 (d, H, J = 8.3 Hz,
2
−
1 1
1
1
2
613, 1490, 850 cm ; H NMR (400 MHz, DMSO-d ):
6
ArH), 7.63 (dd, H, J = 8.3 & 2.2 Hz, ArH); EIMS (m/z) =
.07 (s, 3H, CH ), 1.12 (s, 3H, CH ), 2.26 (s, 2H, CH ),
3
3
2
3
55 (M+1).
-amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(4-
bromophenyl)-5-oxo-4H-chromene-3-carbonitrile (4i).
.46–2.48 (m, 2H, CH ), 4.43 (s, 1H, CH), 6.58 (s, 2H,
2
2
NH ), 7.18–7.28 (m, 4H, ArH); MS (m/z) = 328 (M + 1).
2
2
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(4-
flurophenyl)-5-oxo-4H-chromene-3- carbonitrile (4c).
IR (KBr, cm ): 3400, 3300, 3040, 2990, 2240, 1680,
510, 840 cm ; H NMR (400 MHz, DMSO-d ): 1.03
−
1
−1
IR (KBr, cm ): 3245, 2240, 1623, 1490 cm ; 1H NMR
400 MHz, DMSO-d ): 1.09 (s, 3H, CH ), 1.14 (s, 3H,
(
−
1
6
3
CH ), 2.31 (s, 2H, CH ), 2.25–2.32 (m, 2H, CH ), 4.56
−
1
1
3
2
2
1
(
2
(
6
(
s, 1H, CH), 5.91 (s, 2H, NH ), 7.23–7.41 (m, 4H, ArH);
2
s, 3H, CH ), 1.11 (s, 3H, CH ), 2.21 (d, J = 16.0Hz, 1H),
3 3
EIMS (m/z) =374 (M+1).
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(2-
hydroxyphenyl)-5-oxo-4H-chromene-3-carbonitrile
.22 (d, J =16.0Hz, 1H), 2.43 (s, 2H), 3.77 (s, 3H), 4.36
2
s, 3H), 4.55 (s, 2H), 6.84 (d, J = 8.7Hz, 2H), 7.15 (d, J =
.7Hz, 2H); MS (m/z) = 324 (M + 1).
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(4-
methylphenyl)-5-oxo-4H-chromene-3- carbonitrile
8
−1
−1
(
1
4j). IR (KBr, cm ): 3450, 3290, 2265, 1643, 1460 cm ;
H NMR (400 MHz, DMSO-d ): 1.03 (s, 3H, CH ), 1.23
(s, 3H, CH ), 2.43 (s, 2H, CH ), 2.57–2.71 (m, 2H, CH ),
4.56 (s, 1H, CH), 6.89 (s, 2H, NH ), 7.47–7.87 (m, 4H,
2
6
3
−
1
−1
(
1
4d). IR (KBr, cm ): 3309, 2940, 2210, 1620 cm ;
H NMR (400 MHz, DMSO-d ): 1.15 (s, 3H, CH ), 1.11
3 2 2
2
6
3
ArH); MS (m/z) = 311 (M+1).
(
s, 3H, CH ), 1.17 (s, 3H), 2.87 (s, 2H, CH ), 2.65 (m,
3
2
2
H, CH ), 5.34 (s, 1H, CH), 5.92 (s, 2H, NH ), 7.87–8.01
2-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(4-n,n-
dimethylphenyl)-5-oxo-4H-chromene-3- carbonitrile
2
2
(
m, 4H, ArH); MS(m/z) = 309 (M+1).
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(4-
nitrophenyl)-5-oxo-4H-chromene-3-carbonitrile (4e):
−
1
−1
(4k). IR (KBr, cm ): 3236, 2269, 1616, 1420 cm ;
1
H NMR (400 MHz, DMSO-d6): 0.90 (s, 3H, CH3),
2
−
1
0.98 (s, 3H, CH ), 1.67 (s, 6H, CH ), 2.12 (s, 2H, CH ),
IR (KBr, cm ): 3394, 3323, 3213, 2970, 2193, 1683,
1
3 3 2
−
1 1
523, 1365 cm H NMR (400 MHz, DMSO-d ): 0.99
2.41–2.46 (m, 2H, CH ), 4.34 (s, 1H, CH), 5.87 (s, 2H,
6
2
(
s, 3H, CH ), 1.06 (s, 3H, CH ), 2.14 (d, J = 16.0Hz, 1H),
NH ), 7.08–7.32 (m, 4H, ArH); MS (m/z) = 338 (M+1).
3
3
2
2
.30 (d, J =16.0Hz, 1H), 2.53–2.57 (m, 2H, CH ), 4.39
2
2-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(2-
(s, 1H), 7.24 (s, 2H, NH ), 7.48 (d, 2H, J = 8.4 Hz, ArH),
2
nitrophenyl)-5-oxo-4H-chromene-3-carbonitrile (4l):
8
.21 (s, J = 8.4 Hz, 2H, ArH); MS (m/z) = 339 (M + 1).
-Amino-5,6,7,8-tetrahydro-7,7-dimethyl-4-(4-
methoxyphenyl)-5-oxo-4H-chromene-3- carbonitrile
−1
−1 1
IR (KBr, cm ): 3334, 2246, 1632, 1460 cm ; H NMR
2
(400 MHz, DMSO-d ): 1.12 (s, 3H, CH ), 1.23 (s, 3H,
6
3
CH ), 2.45 (s, 2H, CH ), 2.76–2.89 (m, 2H, CH ), 5.10
3
2
2
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 90 No. 6 2017