12
M. GHASHANG ET AL.
131.5, 132.4, 132.6, 134.7, 138.1, 148.3, 148.7, 159.1, 163.4 ppm. Found: C, 63.09; H, 3.79;
N, 11.74; S, 8.94% C19H13N3O3S; requires: C, 62.80; H, 3.61; N, 11.56; S, 8.82%.
3.3.1.11. (8Z)-2-amino-8-benzylidene-4,5,7,8-tetrahydro-4-phenylthiopyrano[4,3-b]
1
pyran-3-carbonitrile (Table 2, Product b1). H-NMR (400 MHz, DMSO-d6): δ = 2.97
(d, J = 15.7 Hz, 1H), 3.25 (d, J = 15.7 Hz, 1H), 3.54 (d, J = 15.8 Hz, 1H), 3.69 (d,
J = 15.8 Hz, 1H), 4.11 (s, 1H, CH), 6.56 (s, 2H, NH2), 7.14 (s, 1H) 7.23–7.41 (m, 10H)
ppm; 13C NMR (100 MHz, DMSO-d6): δ = 27.9, 28.7, 43.1, 56.5, 114.7, 120.2, 124.7, 126.8,
127.4, 127.6, 128.3, 128.9, 129.6, 129.9, 136.2, 142.1, 144.9, 159.2 ppm. Found: C, 73.86; H,
5.17; N, 7.89; S, 9.07% C22H18N2OS; requires: C, 73.71; H, 5.06; N, 7.82; S, 8.95%.
3.3.1.12. (8Z)-8-(4-methylbenzylidene)-4-(4-methylphenyl)-2-amino-4,5,7,8-
1
tetrahydrothiopyrano[4,3-b]pyran-3-carbonitrile (Table 2, Product b2). H-NMR
(400 MHz, DMSO-d6): δ = 2.25 (s, 3H, CH3), 2.36 (s, 3H, CH3), 2.96 (d, J = 15.9 Hz,
1H), 3.22 (d, J = 15.9 Hz, 1H), 3.57 (d, J = 16.1 Hz, 1H), 3.75 (d, J = 16.1 Hz, 1H), 4.16
(s, 1H, CH), 6.83 (s, 2H, NH2), 7.05–7.27 (m, 9H) ppm; 13C NMR (100 MHz, DMSO-d6):
δ = 21.3, 21.5, 40.9, 43.7, 56.8, 113.9, 120.4, 121.4, 126.9, 127.6, 128.7, 129.1, 129.6, 132.7,
136.9, 140.1, 144.8, 145.1, 153.4, 160.1 ppm. Found: C, 74.77; H, 6.02; N, 7.41; S, 8.49%
C24H22N2OS; requires: C, 74.58; H, 5.74; N, 7.25; S, 8.30%.
3.3.1.13. (8Z)-8-(4-methoxybenzylidene)-4-(4-methoxyphenyl)-2-amino-4,5,7,8-
1
tetrahydrothiopyrano[4,3-b]pyran-3-carbonitrile (Table 2, Product b2). H-NMR
(400 MHz, DMSO-d6): δ = 2.97 (d, J = 15.8 Hz, 1H), 3.24 (d, J = 15.8 Hz, 1H), 3.59 (d,
J = 15.9 Hz, 1H), 3.78 (d, J = 15.9 Hz, 1H), 3.80 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.11
(s, 1H, CH), 6.85–6.98 (m, 6H), 7.14–7.22 (m, 5H) ppm; 13C NMR (100 MHz, DMSO-d6):
δ = 41.2, 43.7, 55.8, 56.7, 56.9, 113.7, 120.5, 121.4, 124.8, 125.3. 127.6, 129.1, 129.6, 136.9,
140.1, 145.1, 153.4, 156.7, 157.9, 160.1 ppm. Found: C, 69.07; H, 5.52; N, 6.93; S, 7.84%
C24H22N2O3S; requires: C, 68.88; H, 5.30; N, 6.69; S, 7.66%.
3.3.1.14. (8Z)-8-(4-tert-butylbenzylidene)-4-(4-tert-butylphenyl)-2-amino-4,5,7,8-
1
tetrahydrothiopyrano[4,3-b]pyran-3-carbonitrile (Table 2, Product b4). H-NMR
(400 MHz, DMSO-d6): δ = 1.26 (s, 9H), 1.37 (s, 9H), 3.00 (d, J = 16.0 Hz, 1H), 3.28 (d,
J = 16.0 Hz, 1H), 3.55 (d, J = 16.2 Hz, 1H), 3.73 (d, J = 16.2 Hz, 1H), 4.17 (s, 1H, CH),
6.77 (s, 2H, NH2), 6.99–7.14 (m, 7H), 7.23 (d, J = 7.8 Hz, 2H) ppm; 13C NMR (100 MHz,
DMSO-d6): δ = 28.1, 29.3, 31.2, 31.5, 34.7, 35.2, 43.4, 57.1, 115.1, 120.2, 125.4, 125.7, 126.8,
128.7, 129.2, 130.0, 131.9, 137.0, 140.2, 144.8, 145.1, 153.4, 159.2 ppm. Found: C, 76.79; H,
7.56; N, 6.21; S, 6.99% C30H34N2OS; requires: C, 76.56; H, 7.28; N, 5.95; S, 6.81%.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
We are thankful to the Islamic Azad University, Najafabad Branch research council for partial
support of this research.