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Typical Procedure: Preparation of Compounds 5, 7 and 10.
The reactions were performed in a monomodal EmrysTM Creator from Personal Chemistry, Uppsala, Sweden. In an EmrysTM reaction vial (10 mL), arylidenemalononitrile (2, 1 mmol), 1,3-indenodione (3, 1 mmol) or dimedone (8, 1 mmol), aromatic amine (4, 1.2 mmol) or aliphatic amine (6, 1.2 mmol) and DMF (1.0 mL) were mixed and then capped. The mixture was irradiated for 4-9 min at 120 °C under microwave irradiation (initial power 100 W and maximum power 200 W). Upon completion of the reaction as monitored by TLC, the reaction mixture was cooled to r.t. and then poured into cold H2O. The solid product was filtered, washed with H2O and EtOH (95%). The solid was purified by recrystallization from EtOH (95%). Spectral data and elemental analyses of selected compounds are given here.
Compound 5g: IR (KBr): ν = 3301, 2208, 1711, 1606, 1559, 1497, 1387, 1329, 753, 704 cm-1. 1H NMR (DMSO-d
6): δ = 9.92 (s, 1 H, NH), 7.95 (d, 1 H, J = 4.8 Hz, thiophenyl-H), 7.71 (t, 4 H, J = 7.6 Hz, ArH), 7.65-7.58 (m, 3 H, ArH), 7.44 (t, 2 H, J = 8.0 Hz, ArH), 7.29 (t, 1 H, J = 4.4 Hz, thiophenyl-H), 7.23-7.20 (m, 1 H, thiophenyl-H) ppm. Anal. Calcd for C23H13N3OS: C, 72.80; H, 3.45; N, 11.07; S, 8.45. Found: C, 72.97; H, 3.34; N, 11.21; S, 8.34.
Compound 5k: IR (KBr): ν = 3306, 2213, 1713, 1610, 1571, 1520, 1240, 1009, 813, 763 cm-1. 1H NMR (DMSO-d
6): δ = 9.90 (s, 1 H, NH), 7.76 (d, 2 H, J = 8.4 Hz, ArH), 7.70-7.68 (m, 2 H, ArH), 7.61-7.60 (m, 2 H, ArH), 7.58 (d, 2 H, J = 8.4 Hz, ArH), 7.53 (d, 2 H, J = 8.4 Hz, ArH), 7.24 (d, 2 H, J = 8.4 Hz, ArH), 2.35 (s, 3 H, CH3) ppm. Anal. Calcd for C26H16BrN3O: C, 66.97; H, 3.46; N, 9.01. Found: C, 66.89; H, 3.54; N, 9.17.
Compound 7a: IR (KBr): ν = 3437, 3335, 2218, 1702, 1621, 1572, 1355, 1201, 1007, 749; 656 cm-1. 1H NMR (DMSO-d
6): δ = 7.74 (d, 2 H, J = 8.4 Hz, ArH), 7.67-7.65 (m, 2 H, ArH), 7.58-7.56 (m, 2 H, ArH), 7.57 (d, 2 H, J = 8.4 Hz, ArH), 5.46 (s, 2 H, NH2), 4.98 (s, 1 H, CH) ppm. Anal. Calcd for C19H11BrN2O2: C, 60.18; H, 2.92; N, 7.39. Found: C, 60.35; H, 2.74; N, 7.25.
