## 2 Experimental
### General Procedure for Synthesis of N-methyl-3-aryl imidazole (5a-5j) (Route 2)
101-103 \({}^{\circ}\)C; IR (KBr, \(v_{\rm max}\),cm\({}^{-1}\)): 3052(Ar=CH str), 2925 (CH str), 1612, 1508, 1459(Ar=C str), 1390 (C=N str), 1205(N-N str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 8.71 (d, 2H, \(J\) = 8.5 Hz, ArH), 8.06 (d, 1H, \(J\) = 8.0 Hz, ArH), 7.92 (d, 2H, \(J\) = 7.5 Hz, Ar-H), 7.42 (d, J = 7.0 Hz, 2H, ArH); 7.26 (m, 1H, ArH), 4.19 (s, 3H, CH\({}_{3}\)); \({}^{13}\)C NMR (75 MHz, CDCl\({}_{3}\)): \(\delta\) = 166.1, 160.7, 145.7, 135.2, 132.2, 128.7, 128.6, 128.1, 127.9, 126.5, 36.4; _m/z_ (ESI-MS) 210.41 (M + H)\({}^{+}\). _1-Methyl-3-(pyridin-3-yl)-1H-inadazole_ **(5e)**: m.p. 74-76 \({}^{\circ}\)C; IR (KBr, \(v_{\rm max}\), cm\({}^{-1}\)): 3136 (Ar=CH str), 2949, 2873 (CH str), 1593, 1534(Ar=C str), 1348 (C=N str), 1189 (N-N str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 9.22 (s, 1H, ArH), 8.62 (s, 1H, ArH), 8.36 (dd, 1H, \(J\) = 7.5 Hz, ArH), 8.02 (d, \(J\) = 7.0 Hz, 1H, ArH); 7.51 (m, 3H, ArH), 7.32 (s, 1H, ArH). 4.18 (s, 3H, CH\({}_{3}\)); \({}^{13}\)C NMR (100 MHz, DMSO-d6) \(\delta\) = 153.6, 149.8, 141.9, 141.9, 141.8, 137.3, 126.9, 123.7, 122.9, 122.0, 120.5, 110.4, 36.2; _m/z_ (ESI-MS) 210.29 (M + H)\({}^{+}\). _3-(4-Methoxyphenyl)-1-methyl-1H-inadazole_ **(5f)**: m.p. 112-114 \({}^{\circ}\)C;IR (KBr, \(v_{\rm max}\), cm\({}^{-1}\)): 3098 (Ar=CH str), 2960, 2921, 2872 (CH str), 1607, 1569, 1530(Ar=C str), 1350 (C=N str), 1201 (N-N str), 1164 (C-O-C str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 8.02 (d, \(J\) = 8.0 Hz, 1H, ArH), 7.90 (d, 2H, \(J\) = 8.5 Hz, ArH), 7.42 (m, 2H, ArH), 7.23 (m, 1H, ArH); 7.08 (d, \(J\) = 8.5, 2H, ArH), 4.15 (s, 3H, OCH\({}_{3}\)), 3.91 (s, 3H, NCH\({}_{3}\)); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \({}^{13}\)C NMR (100 MHz, DMSO-d6) \(\delta\) = 159.4, 142.4, 141.6, 128.4, 126.6, 126.4, 121.3, 121.0, 114.8, 110.5, 55.7, 35.9; _m/z_ (ESI-MS) 239.09 (M + H)\({}^{+}\). _1-Methyl-3-(4-(methylthio)phenyl)-1H-inadazole_ **(5g)**: m.p. 99-101 \({}^{\circ}\)C; IR (KBr, \(v_{\rm max}\), cm\({}^{-1}\)): 3095 (Ar=CH str), 2956, 2922, 2864 (CH str), 1625, 1582, 1495 (ArC=C str), 1384 (C=N str), 1234 (N-N str), 1157 (C-S-C str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 8.01 (d, \(J\) = 7.5 Hz, 1H, ArH), 7.89 (d, 2H, \(J\) = 8.0 Hz, ArH), 7.41 (m, 4H, ArH), 7.20 (m, 1H, ArH); 4.14 (s, 3H, NCH\({}_{3}\)), 2.58 (s, 3H, NCH\({}_{3}\)); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) = 166.4, 160. 6, 145.7, 135.2, 132.2, 131.7, 128.6, 128.1, 127.9, 126.5, 119.7, 55.4, 36.3; _m/z_ (ESI-MS) 255.32 (M + H)\({}^{+}\). _3-(2-Methoxyphenyl)-1-methyl-1H-inadazole_ **(5h)**: m.p. 105-107 \({}^{\circ}\)C; IR (KBr, \(v_{\rm max}\), cm\({}^{-1}\)): 3053.97b (Ar=CH str), 2955, 2894 (CH str), 1614, 1520, 1459(ArC=C str), 1372 (C=N str), 1278 (N-N str), 1172 (C-O-C str); \({}^{1}\)H NMR (300 MHz, CDCl\({}_{3}\)): \(\delta\) 8.01 (d, \(J\) = 9.0 Hz, 1H, ArH), 7.78 (d, 1H, \(J\) = 8.5 Hz, ArH), 7.41 (m, 3H, ArH), 7.05-7.18 (m, 3H, ArH); 4.16 (s, 3H, OCH\({}_{3}\)): 3.82 (s, 3H, NCH\({}_{3}\)); \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)): \(\delta\) = 161.7, 143.6, 141.7, 137.6, 132.9, 132.2, 128.9, 128.1, 128.6, 123.3, 120.4, 116.0, 110.5, 55.2, 35.2; _m/z_ (ESI-MS) 239.33 (M + H)\({}^{+}\). _4-(1-Methylthiazol-3-yl)phenol_ **(5i)**: m.p. 241-243 \({}^{\circ}\)C; IR (KBr, \(v_{\rm max}\), cm\({}^{-1}\)): 3691(OH str), 3439 (NH str), 2991 (Ar=CH str), 2897 (CH str), 1601, 1545, 1498 (ArC=C str), 1449 (C=N str), 1233 (N-N str); \({}^{1}\)H NMR (400 MHz, DMSO-d6) \(\delta\) 4.06 (3H, s) 6.93 (2H, d, \(J\) = 8.6 Hz) 7.18 (1H, t, \(J\) = 7.5 Hz) 7.42 (1H, t, \(J\) = 7.6 Hz) 7.62 (1H, d, \(J\) = 8.6 Hz) 7.80 (2H, d, \(J\) = 8.6 Hz) 8.00 (1H, d, \(J\) = 8.2 Hz) 9.65 (1H, s); \({}^{13}\)C NMR (100 MHz, DMSO-d6) \(\delta\) = 157.7, 142.8, 141.6, 128.5, 126.5, 124.8, 121.4, 121.2, 120.9, 116.2, 110.3, 35.8; _m/z_ (ESI-MS) 225.10 (M + H)\({}^{+}\). _N,N-Dimethyl-4-(1-methyl-1H-inadazol-3-yl)benzamide_ **(5j)**: m.p.