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, 𝜈, cm^−1	^1HNMR spectrum (200 MHz, DMSO), 𝛿, ppm (𝐽, Hz)	Mass spectrum (EI, 70 eV), 𝑚/𝑧 (Irel, %)
3a	2933 (CH2); 2227, 2220 (2CN); 1634 (C=C)	1.34–2.44 (m, 8H, 4CH2)	132 (M^+, 15%)
3b	2936, 2890 (CH3, CH2); 2222 (CN); 1688 (C=O), 1634 (C=C)	1.13 (t, 3H, 𝐽=7.01 Hz, CH3), 1.36–2.40 (m, 8H, 4CH2), 4.22 (q, 2H, 𝐽=7.01 Hz, CH2)	179 (M^+, 22%)
5a	2936 (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%)
5b	3055 (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%).
5c	3058 (CH aromatic), 2946 (CH2), 2220 (CN), 1632 (C=C)	1.13 (t, 3H, 𝐽=7.22 Hz, CH3), 1.30–2.38 (m, 6H, 3CH2), 4.25 (q, 2H, 𝐽=7.22, CH2), 7.26–7.36 (m, 5H, C6H5), 8.36 (s, 1H, NH)	283 (M^+, 40%)
5d	3060 (CH aromatic), 2923, 2891 (CH3, CH2), 2222 (CN), 1636 (C=C).	1.12 (t, 3H, 𝐽=7.03 Hz, CH3), 1.32–2.41 (m, 6H, 3CH2), 4.22 (q, 2H, 𝐽=7.03 Hz, CH2), 7.28–7.40 (m, 5H, C6H5), 8.42 (s, 1H, NH)	317 (M^+, 35%)
7a	3456–3435 (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%)
7b	3466–3465 (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%)
7c	3566–3425 (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%).
7d	3520–3435 (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%).
9a	3058 (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%).
9b	3056 (CH aromatic), 2923 (CH2), 2223 (CN), 1688 (C=O), 1663 (C=C).	1.12 (t, 3H, 𝐽=7.05 Hz, CH3), 1.32–2.34 (m, 6H, 3CH2), 4.22 (q, 2H, 𝐽=7.05 Hz, CH2), 6.03 (s, 1H, C=CH), 7.28–7.40 (m, 5H, C6H5)	267 (M^+, 15%).
11a	3466–3321 (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%)
11b	3448–3318 (NH2), 3058 (CH aromatic), 2933 (CH2), 2220 (CN), 1690 (C=O), 1638 (C=C).	1.12 (t, 3H, 𝐽=6.94 Hz, CH3), 1.28–2.37(m, 6H, 3CH2), 4.22 (q, 2H, 𝐽=6.94 Hz, CH2), 4.48 (s, 2H, NH2), 7.28–7.39 (m, 5H, C6H5)	306 (M^+, 22%)
11c	3453–3322 (NH2), 3055 (CH aromatic), 2931 (CH2), 2222 (CN), 1690 (C=O), 1638 (C=C)	1.12 (t, 3H, 𝐽=6.94 Hz, CH3), 1.26–2.37 (m, 6H, 3CH2), 4.24 (q, 2H, 𝐽=6.94 Hz, CH2), 4.49 (s, 2H, NH2), 7.26–7.38 (m, 5H, C6H5)	306 (M^+, 22%)
11d	3460–3342 (NH2), 3050 (CH aromatic), 2930 (CH2), 1688, 1690 (2 C=O), 1636 (C=C).	1.13, 1.15 (2t, 6H, 𝐽=6.66, 7.15 Hz, 2CH3), 1.28–2.39 (m, 6H, 3CH2), 4.21, 4.25 (q, 4H, 𝐽=6.66, 7.15 Hz, 2CH2), 4.46 (s, 2H, NH2), 7.29–7.39 (m, 5H, C6H5)	353 (M^+, 22%)
13a	3453–3321 (NH2), 3056 (CH aromatic), 2940 (CH2), 1633 (C=C).	1.22–2.38 (m, 6H, 3CH2), 4.43 (s, 2H, NH2)	164 (M^+, 100%)
13b	3466–3348 (NH2), 3055 (CH aromatic), 2936, 2884 (CH3, CH2), 1689 (C=O), 1638 (C=C).	1.12 (t, 3H, 𝐽=7.22 Hz, CH3), 1.25–2.36 (m, 6H, 3CH2), 4.22 (q, 2H, 𝐽=7.22 Hz, CH2), 4.46 (s, 2H, NH2)	211 (M^+, 100%)
14a	3453–3321 (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%).
14b	3465–3342 (NH2, NH), 3058 (CH aromatic), 2936, 2841 (CH3, CH2), 1694(C=O), 1663 (C=C).	1.12 (t, 3H, 𝐽=7.44 Hz, CH3), 1.24–2.36 (m, 4H, 2CH2), 4.22 (q, 2H, 𝐽=7.44 Hz, CH2), 4.52 (s, 2H, NH2), 7.27–7.44 (m, 5H, C6H5), 8.63 (s, 1H, NH)	315 (M^+, 100%)
15a	3453–3321 (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%)
15b	3466–3341 (NH2), 3057 (CH aromatic), 2940, 2877 (CH3, CH2), 1684, 1689 (2C=O), 1639 (C=C).	1.14 (t, 3H, 𝐽=7.42 Hz, CH3), 1.20–2.37 (m, 4H, 2CH2), 2.68; (s, 3H, CH3), 4.22 (q, 2H, 𝐽=7.42 Hz, CH2), 7.28–7.39 (m, 5H, C6H5), 8.38, 8.52 (2s, 2H, 2NH)	357 (M^+, 38%)
16a	3477, 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%)
16b	3050 (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%)