Journal of Chemistry / 2013 / Article / Tab 2

Research Article

The Reaction of Cyclopentanone with Cyanomethylene Reagents: Novel Synthesis of Pyrazole, Thiophene, and Pyridazine Derivatives

Table 2

Spectral data of the newly synthesized products.

Comp.IR spectrum, , cm−1 1HNMR spectrum (200 MHz, DMSO), , ppm ( , Hz)Mass spectrum (EI, 70 eV), (Irel, %)

3a2933 (CH2); 2227, 2220 (2CN); 1634 (C=C)1.34–2.44 (m, 8H, 4CH2)132 (M+, 15%)

3b2936, 2890 (CH3, CH2); 2222 (CN); 1688 (C=O), 1634 (C=C)1.13 (t, 3H,  Hz, CH3), 1.36–2.40 (m, 8H, 4CH2), 4.22 (q, 2H,  Hz, CH2)179 (M+, 22%)

5a2936 (CH2), 3058 (CH aromatic), 2228, 2220 (2CN); 1636 (C=C)1.36–2.41 (m, 6H, 3CH2), 7.27–7.37 (m, 5H, C6H5), 8.77 (s, 1H, NH)236 (M+, 18%)

5b3055 (CH aromatic), 2940 (CH2), 2228, 2222 (2CN), 1630 (C=C)1.32–2.39 (m, 6H, 3CH2), 7.29–7.39 (m, 4H, C6H4), 8.33 (s, 1H, NH)270 (M+, 77%).

5c3058 (CH aromatic), 2946 (CH2), 2220 (CN), 1632 (C=C)1.13 (t, 3H,  Hz, CH3), 1.30–2.38 (m, 6H, 3CH2), 4.25 (q, 2H, , CH2), 7.26–7.36 (m, 5H, C6H5), 8.36 (s, 1H, NH)283 (M+, 40%)

5d3060 (CH aromatic), 2923, 2891 (CH3, CH2), 2222 (CN), 1636 (C=C).1.12 (t, 3H,  Hz, CH3), 1.32–2.41 (m, 6H, 3CH2), 4.22 (q, 2H,  Hz, CH2), 7.28–7.40 (m, 5H, C6H5), 8.42 (s, 1H, NH)317 (M+, 35%)

7a3456–3435 (2 NH2), 3058 (CH aromatic), 2942 (CH2), 1667 (exocyclic C=N), 1638 (C=C)1.32–2.36 (m, 6H, 3CH2), 2.81 (t, 1H, CH), 4.21, 4.85 (2s, 4H, 2NH2), 7.29–7.40 (m, 5H, C6H5), 8.38, 9.01 (2s, 2H, 2NH) 270 (M+, 28%)

7b3466–3465 (2 NH2), 3052 (CH aromatic), 2938 (CH2), 1668 (exocyclic C=N), 1632 (C=C).1.33–2.38 (m, 6H, 3CH2), 2.80 (t, 1H, CH), 4.23, 4.86 (2s, 4H, 2NH2), 7.25–7.48 (m, 10H, 2C6H5), 8.35, 8.88 (1s, 1H, 1NH).346 (M+, 21%)

7c3566–3425 (OH, NH2), 3053 (CH aromatic), 2934 (CH2), 1666 (excyclic C=N), 1631 (C=C). 1.32–2.36 (m, 6H, 3CH2), 2.82 (t, 1H, CH), 4.21, 4.85 (2s, 4H, NH2), 7.30–7.38 (m, 5H, C6H5), 8.33 (s, 1H, NH), 10.22 (OH)271 (M+, 21%).

7d3520–3435 (OH, NH2), 3050 (CH aromatic), 2931 (CH2), 1670 (exocyclic C=N), 1634 (C=C). 1.33–2.38 (m, 6H, 3CH2), 2.80 (t, 1H, CH), 4.23, 4.86 (2s, 2H, NH2), 7.32–7.37 (m, 10H, 2 C6H5), 8.32 (s, 1H, NH), 10.20 (OH)347 (M+, 18%).

9a3058 (CH aromatic), 2920 (CH2), 2227–2220 (2 CN), 1660 (C=C). 1.30–2.38 (m, 6H, 3CH2), 6.01 (s, 1H, C=CH), 7.28–7.37 (m, 5H, C6H5)220 (M+, 18%).

9b3056 (CH aromatic), 2923 (CH2), 2223 (CN), 1688 (C=O), 1663 (C=C). 1.12 (t, 3H,  Hz, CH3), 1.32–2.34 (m, 6H, 3CH2), 4.22 (q, 2H,  Hz, CH2), 6.03 (s, 1H, C=CH), 7.28–7.40 (m, 5H, C6H5) 267 (M+, 15%).

11a3466–3321 (NH2), 3060 (CH aromatic), 2929 (CH2), 2228, 2222 (2 CN), 1636 (C=C).1.30–2.36 (m, 6H, 3CH2), 4.48 (s, 2H, NH2), 7.26–7.38 (m, 5H, C6H5)259 (M+, 15%)

11b3448–3318 (NH2), 3058 (CH aromatic), 2933 (CH2), 2220 (CN), 1690 (C=O), 1638 (C=C). 1.12 (t, 3H,  Hz, CH3), 1.28–2.37(m, 6H, 3CH2), 4.22 (q, 2H,  Hz, CH2), 4.48 (s, 2H, NH2), 7.28–7.39 (m, 5H, C6H5) 306 (M+, 22%)

11c3453–3322 (NH2), 3055 (CH aromatic), 2931 (CH2), 2222 (CN), 1690 (C=O), 1638 (C=C)1.12 (t, 3H,  Hz, CH3), 1.26–2.37 (m, 6H, 3CH2), 4.24 (q, 2H,  Hz, CH2), 4.49 (s, 2H, NH2), 7.26–7.38 (m, 5H, C6H5)306 (M+, 22%)

11d3460–3342 (NH2), 3050 (CH aromatic), 2930 (CH2), 1688, 1690 (2 C=O), 1636 (C=C).1.13, 1.15 (2t, 6H, , 7.15 Hz, 2CH3), 1.28–2.39 (m, 6H, 3CH2), 4.21, 4.25 (q, 4H, , 7.15 Hz, 2CH2), 4.46 (s, 2H, NH2), 7.29–7.39 (m, 5H, C6H5) 353 (M+, 22%)

13a3453–3321 (NH2), 3056 (CH aromatic), 2940 (CH2), 1633 (C=C). 1.22–2.38 (m, 6H, 3CH2), 4.43 (s, 2H, NH2)164 (M+, 100%)

13b3466–3348 (NH2), 3055 (CH aromatic), 2936, 2884 (CH3, CH2), 1689 (C=O), 1638 (C=C). 1.12 (t, 3H,  Hz, CH3), 1.25–2.36 (m, 6H, 3CH2), 4.22 (q, 2H,  Hz, CH2), 4.46 (s, 2H, NH2)211 (M+, 100%)

14a3453–3321 (NH2), 3056 (CH aromatic), 2940 (CH2), 1633 (C=C). 29–7.36 (m, 5H, C6H5), 8.23 (s, 1H, NH). 1.22–2.38 (m, 4H, 4CH2), 4.43 (s, 2H, NH2), 7.29–7.36 (m, 5H, C6H5), 8.23 (s, 1H, NH)268 (M+, 100%).

14b3465–3342 (NH2, NH), 3058 (CH aromatic), 2936, 2841 (CH3, CH2), 1694(C=O), 1663 (C=C).1.12 (t, 3H,  Hz, CH3), 1.24–2.36 (m, 4H, 2CH2), 4.22 (q, 2H,  Hz, CH2), 4.52 (s, 2H, NH2), 7.27–7.44 (m, 5H, C6H5), 8.63 (s, 1H, NH) 315 (M+, 100%)

15a3453–3321 (NH2), 3060 (CH aromatic), 2942, 2893 (CH3, CH2), 2220 (CN), 1685 (C=O), 1636 (C=C). 1.20–2.35 (m, 4H, 2CH2), 2.62 (s, 3H, CH3), 7.28–7.40 (m, 5H, C6H5), 8.40, 8.63 (2s, 2H, 2NH)310 (M+, 60%)

15b3466–3341 (NH2), 3057 (CH aromatic), 2940, 2877 (CH3, CH2), 1684, 1689 (2C=O), 1639 (C=C).1.14 (t, 3H,  Hz, CH3), 1.20–2.37 (m, 4H, 2CH2), 2.68
(s, 3H, CH3), 4.22 (q, 2H,  Hz, CH2), 7.28–7.39 (m, 5H, C6H5), 8.38, 8.52 (2s, 2H, 2NH)
357 (M+, 38%)

16a3477, 3320 (NH), 3054 (CH aromatic), 2936 (CH2), 1663 (exocyclic C=N), 1638 (C=C).1.22–2.39 (m, 6H, 3CH2), 7.32–7.43 (m, 5H, C6H5), 8.36 (s, 1H, NH)236 (M+, 100%)

16b3050 (CH aromatic), 2940 (CH2), 1687 (C=O), 1644 (C=C). 1.25–2.36 (m, 6H, 3CH2), 7.30–7.48 (m, 5H, C6H5)237 (M+, 100%)

Article of the Year Award: Outstanding research contributions of 2020, as selected by our Chief Editors. Read the winning articles.