JOURNAL OF SULFUR CHEMISTRY
7
4.2.4. (Z)-2-Amino-8-(4-methoxybenzylidene)-4-(4-methoxyphenyl)-4,5,7,8-
tetrahydrothiopyrano[4,3-b]pyran-3-carbonitrile (3e)
1
Mp 192–193°C; IR (KBr, cm−1) 3403, 3321, 2191 (C≡N), 1670 (C C), 1414; HNMR
(DMSO-d6, 500 MHz) δ 2.84 (d, J = 17.0 Hz, 1H, CHS), 3.17 (d, J = 17.0 Hz, 1H, CHS),
3.55 (d, J = 15.0 Hz, 1H, CHS), 3.62 (d, J = 15.0 Hz, 1H, CHS), 3.70 (s, 3H, Me), 3.73 (s,
3H, Me), 3.96 (s, 1H, CHAr), 6.75 (s, 2H, NH2), 6.88 (d, J = 8.5 Hz, 2H, 2 arom. H), 6.94
=
=
(d, J = 8.5 Hz, 2H, 2 arom. H), 7.04 (s, 1H, CH), 7.09 (d, J = 8.5 Hz, 2H, 2 arom. H),
7.23 (d, J = 8.5 Hz, 2H, 2 arom. H) ppm; 13CNMR (DMSO-d6, 125 MHz) δ 27.2 (CH2S),
28.1 (CH2S), 43.3, 55.9 (Me), 56.0 (Me), 57.2, 114.4, 114.9, 115.0, 121.2, 125.0, 125.6, 129.1,
129.5, 131.5, 136.4, 142.2, 159.3, 159.4, 160.4 ppm; MS (70 eV): m/z 418 (M+), 368, 311,
238, 111; Anal. Calcd for C24H22N2O3S: C, 68.88; H, 5.30; N, 6.69. found: C, 69.01; H, 5.45;
N, 6.72.
4.2.5. (Z)-2-Amino-8-(4-(methylthio)benzylidene)-4-(4-(methylthio)phenyl)-4,5,7,8-
tetrahydrothiopyrano[4,3-b]pyran-3-carbonitrile (3f)
1
Mp 222–223°C; IR (KBr, cm−1) 3472, 3325, 2183 (C≡N), 1665 (C C), 1406; HNMR
=
(DMSO-d6, 500 MHz) δ 2.48 (s, 3H, Me), 2.50 (s, 3H, Me), 2.91 (d, J = 17.0 Hz, 1H, CHS),
3.24 (d, J = 17.0 Hz, 1H, CHS), 3.61 (d, J = 15.0 Hz, 1H, CHS), 3.66 (d, J = 15.0 Hz, 1H,
=
CHS), 4.05 (s, 1H, CHAr), 6.87 (s, 2H, NH2), 7.10 (s, 1H, CH), 7.17 (d, J = 8.0 Hz, 2H, 2
arom. H), 7.26 (d, J = 8.0 Hz, 2H, 2 arom. H), 7.28–7.29 (m, 4H, 4 arom. H) ppm; 13CNMR
(DMSO-d6, 125 MHz) δ 27.0 (CH2S), 28.0 (CH2S), 43.4, 55.9, 115.0, 120.9, 124.2, 127.9,
129.4, 129.6, 130.3, 131.8, 132.7, 132.9, 135.6, 142.3, 143.2, 160.5 ppm; MS (70 eV): m/z 450
(M+), 368, 311, 238, 137; Anal. Calcd. for C24H22N2OS3: C, 63.97; H, 4.92; N, 6.22. found:
C, 64.14; H, 4.76; N, 6.39.
4.2.6. (Z)-2-Amino-4-(furan-2-yl)-8-(furan-2-ylmethylene)-4,5,7,8-
tetrahydrothiopyrano[4,3-b]pyran-3-carbonitrile (3g)
1
Mp 240–241°C; IR (KBr, cm−1) 3437, 3320, 2196 (C≡N), 1667 (C C), 1418; HNMR
=
(DMSO-d6, 500 MHz) δ 3.12 (d, J = 17.0 Hz, 1H, CHS), 3.29 (d, J = 17.0 Hz, 1H, CHS),
3.80 (d, J = 15.5 Hz, 1H, CHS), 3.94 (d, J = 15.5 Hz, 1H, CHS), 4.26 (s, 1H, CHAr),
6.24 (d, J = 3.0 Hz, 1H, 1 arom. H), 6.40 (dd, J = 2.0, 3.0 Hz, 1H, 1 arom. H), 6.60 (d,
J = 2.0 Hz, 1H, 1 arom. H), 6.62 (d, J = 3.0 Hz, 1H, 1 arom. H), 6.90 (s, 1H, 1 arom. H),
6.95 (s, 2H, NH2), 7.59 (s, 1H, CH), 7.78 (s, 1H, 1 arom. H) ppm; 13CNMR (DMSO-d6,
=
125 MHz) δ 27.3 (CH2S), 27.9 (CH2S), 37.7, 53.9, 107.5, 111.3, 112.6, 113.0, 113.1, 113.8,
120.9, 124.1, 142.9, 143.6, 144.7, 152.3, 155.5, 161.2 ppm; MS (70 eV): m/z 338 (M+), 257,
236, 111; Anal. Calcd. for C18H14N2O3S: C, 63.89; H, 4.17; N, 8.28. found: C, 63.55; H,
4.37; N, 8.17.
4.2.7. (Z)-2-Amino-4-(thiophen-2-yl)-8-(thiophen-2-ylmethylene)-4,5,7,8-
tetrahydrothiopyrano[4,3-b]pyran-3-carbonitrile (3h)
1
Mp 242–243°C; IR (KBr, cm−1) 3427, 3311, 2191 (C≡N), 1662 (C C); HNMR (DMSO-
=
d6, 500 MHz) δ 3.12 (d, J = 17.0 Hz, 1H, CHS), 3.31 (d, J = 17.0 Hz, 1H, CHS), 3.72 (d,
J = 15.0 Hz, 1H, CHS), 3.82 (d, J = 15.0 Hz, 1H, CHS), 4.46 (s, 1H, CHAr), 6.96–6.99 (m,
4H, 2 arom. H & NH2), 7.16 (dd, J = 4.0, 4.5 Hz, 1H, 1 arom. H), 7.22 (d, J = 3.0 Hz, 1H,
=
1 arom. H), 7.29 (s, 1H, CH), 7.44 (d, J = 5.0 Hz, 1H, 1 arom. H), 7.66 (d, J = 5.0 Hz,
1H, 1 arom. H) ppm; 13CNMR (DMSO-d6, 125 MHz) δ 27.3 (CH2S), 27.9 (CH2S), 39.3,