*3.4. Spectroscopic Data*

Compound **3a** *(4-(4 -chlorophenylimino)-2,6-dimethoxycyclohexa-2,5-dienone)* Yield 55.5%. 1H-NMR (CDCl3, 400 MHz) δ 3.668 (s, 3H, H8), 3.870 (s, 3H, H7), 6.040 (d, 1H, *J* = 1.9 Hz, H3), 6.377 (d, 1H, *J* = 1.9 Hz, H5), 6.816 (d, 2H, *J* = 8.5 Hz, H2'), 7.361(d, 2H, *J* = 8.5 Hz, H3'); 13C-NMR (CDCl3, 100 MHz) δ 56.188 (C8), 56.298 (C7), 98.529 (C3), 111.846 (C5), 122.040 (C2'), 129.333 (C3'), 130.749 (C4'), 148.777 (C1'), 154.813 (C6), 155.745 (C2), 157.642 (C4), 176.647 (C1). mp 208.0–209.1 ◦C. GC-MS RI(Rtx-5ms) = 2366, C14H12O3NCl EI-MS *m*/*z*: 111 (15); 150 (16); 178 (15); 182 (17); 197 (35); 212 (15); 224 (22); [M]<sup>+</sup> = 277 (100); [M + 1]<sup>+</sup> = 278 (17); [M + 2]+ = 279 (36).

Compound **3b** (*4-(3 -chlorophenylimino)-2,6-dimethoxycyclohexa-2,5-dienone)* Yield 72.0%. 1H-NMR (CDCl3, 400 MHz) δ 3.670 (s, 3H, H8), 3.874 (s, 3H, H7), 6.010 (d, 1H, *J* = 1.9 Hz, H3), 6.368 (d, 1H, *J* = 1.9 Hz, H5), 6.737 (d, 1H, *J* = 7.9 Hz, H6'), 6.888 (s, 1H, *J* = 8.0 Hz, H2'), 7.159 (d, 1H, *J* = 8,0 Hz, H4'), 7.316 (t, 1H, *J* = 7.9 Hz, H5'); 13C-NMR (CDCl3, 100 MHz) δ 56.212 (C8), 56.321 (C7), 98.583 (C3), 111.717 (C5), 118.705 (C6'), 120.635 (C2'), 125.023 (C4'), 130.247 (C5'), 134.928 (C3'), 151.483 (C1'), 154.881 (C6), 155.741 (C2), 157.816 (C4), 176.633 (C1). mp 155.7–156.0 ◦C. GC-MS RI(Rtx-5ms) = 2340, C14H12O3NCl EI-MS m/z: 69 (22); 75 (52); 111 (58); 113 (21); 140 (20); 178 (26); 182 (24); 197 (43) [M]<sup>+</sup> = 277 (100); [M + 1]<sup>+</sup> = 278 (17); [M + 2]+ =279 (36).

Compound **3c** *(4-(4 -methoxyphenylimino)-2,6-dimethoxycyclohexa-2,5-dienone)* Yield 23.7%. 1H-NMR (CDCl3, 400 MHz) δ 3.691 (s, 3H, H8), 3.846 (s, 3H, H7'), 3.870 (s, 3H, H7), 6.242 (d, 1H, *J* = 1.9 Hz, H3), 6.467 (d, 1H, *J* = 1.9 Hz, H5), 6.903 (d, 2H, *J* = 8.9 Hz, H2'), 6.956 (d, 2H, *J* = 8.9 Hz, H3'); 13C-NMR (CDCl3, 100 MHz) δ 55.656 (C7'), 56.104 (C8), 56.277 (C7), 98.966 (C3), 112.113 (C5), 114.594 (C3'), 123.047 (C2'), 143.196 (C1'), 154.661 (C6), 155.739 (C2), 156.809 (C4), 158.018 (C4'), 176.669 (C1). mp 111.7–112.3 ◦C. GC-MS RI(Rtx-5ms) = 2451, C15H15O4N EI-MS *m*/*z*: 134 (10); 172 (20); 198 (12); 200 (9); 212 (9); 230 (30); 240 (12); 258 (45); [M]<sup>+</sup> = 273 (100); [M + 1]+ = 274 (18).

Compound **3d** *(2,6-dimethoxy-4-(3 -methoxyphenylimino)cyclohexa-2,5-dienone)* Yield 24.24%. 1H-NMR (CDCl3, 400 MHz) δ 3.656 (s, 3H, H8), 3.819 (s, 3H, H7'), 3.868 (s, 3H, H7), 6.125 (d, 1H, *J* = 2.0 Hz, H3), 6.392 (d, 1H, *J* = 2.0 Hz, H5), 6.429 (d, 1H, *J* = 7.7 Hz, H6'), 6.452 (s, 1H, H2'), 6.736 (d, 1H, *J* = 8.1 Hz, H4'), 7.281 (t, 1H, *J* = 8.0 Hz, H5'); 13C-NMR (CDCl3, 100 MHz) δ 55.476 (C7'), 56.124 (C8), 56.248 (C7), 99.051 (C3), 106.387 (C2'), 110.942 (C4'), 112.023 (C5), 112.868 (C6'), 126.946 (C5'), 151.664 (C1'), 154.783 (C6), 155.569 (C2), 157.264 (C4), 160.402 (C3'), 176.785 (C1). mp 133.5–134.6 ◦C. GC-MS RI(Rtx-5ms) = 2403, C15H15O4N EI-MS *m*/*z*: 159 (13); 187 (16); 199 (19); 200 (13); 212 (12); 215 (22); 230 (21); 242 (24) [M]<sup>+</sup> = 273 (100); [M + 1]<sup>+</sup> = 274 (18).

Compound **3e** *(2,6-dimethoxy-4-(4 -nitrophenylimino)cyclohexa-2,5-dienone)* Yield 56.8%. 1H-NMR (CDCl3, 400 MHz) δ 3.660 (s, 3H, H8), 3.895 (s, 3H, H7), 5.845 (d, 1H, *J* = 1.8 Hz, H3), 6.363 (d, 1H, *J* = 1.8 Hz, H5), 6.959 (d, 2H, *J* = 8.8 Hz, H2'), 8.279(d, 2H, *J* = 8.8 Hz, H3'); 13C-NMR (CDCl3, 100 MHz) δ 56.341 (C8), 56.439 (C7), 98.339 (C3), 111.172 (C5), 120.620 (C2'), 125.205 (C3'), 144.864 (C4'), 155.257 (C1'), 156.102 (C6), 156.170 (C2), 157.940 (C4), 176.321 (C1). mp 208.0–209.1 ◦C. GC-MS RI(Rtx-5ms) = 2690, C14H12O5N2 EI-MS *m*/*z*: 16 (33); 128 (21); 143 (29); 156 (25); 168 (18); 169 (20); 197 (38); 211 (26); [M]<sup>+</sup> = 288 (100); [M + 1]<sup>+</sup> = 289 (16).

Compound **3f** *(4-(3 ,4 -dichlorophenylimino)-2,6-dimethoxycyclohexa-2,5-dienone)* Yield 50.4%. 1H-NMR (CDCl3, 400 MHz) δ 3.690 (s, 3H, H8), 3.874 (s, 3H, H7), 5.982 (s, 1H, H3), 6.347 (s, 1H, H5), 6.715 (d, 1H, *J*= 8.4 Hz, H6'), 6.994 (s, 1H, H2'), 7.449 (d, 1H, *J* = 8.4 Hz, H5'); 13C-NMR (CDCl3, 100 MHz) δ 56.319 (C8), 56.355 (C7), 98.322 (C3), 111.572 (C5), 120.097 (C6'), 122.367 (C2'), 128.704 (C3'), 130.913 (C5'), 133.211 (C4'), 149.770 (C1'), 155.033 (C6), 155.973 (C2), 158.242 (C4), 176.486 (C1). mp 160.1–161.5 ◦C. GC-MS RI(Rtx-5ms) = 2556, C14H11O3NCl2 EI-MS m/z: 109 (22); 145 (18); 184 (21); 212 (20); 216 (26); 231 (41); 233 (28); 258 (24); [M]<sup>+</sup> = 311 (100); [M + 2]+ = 313 (65); [M + 4]+ = 315 (13).

Compound **3g** *(4-(4 -(trifluoromethyl)phenylimino)-2,6-dimethoxycyclohexa-2,5-dienone)* Yield 12.7%. 1H-NMR (CDCl3, 400 MHz) δ 3.643 (s, 3H, H8), 3.868 (s, 3H, H7), 5.928 (s, 1H, H3), 6.367 (s, 1H, H5), 6.933 (d, 2H, *J* = 8.1 Hz, H2'), 7.633 (d, 2H, *J* = 8.1 Hz, H3'); 13C-NMR (CDCl3, 100 MHz) δ 56.211 (C8), 56.302 (C7), 98.439 (C3), 111.559 (C5), 120.453 (C2'), 124.319 (q, *J* = 271.6 Hz, C5'), 126.425 (q, *J* = 3.7 Hz, C3'), 126.936 (q, *J* = 32.7 Hz, C4'), 153.272 (C1'), 154.987 (C6), 155.898 (C2), 157.775 (C4), 176.491 (C1). mp 130–133 ◦C. GC-MS RI(Rtx-5ms) = 2084, C15H12O3NF3 EI-MS *m*/*z*: 53 (22); 69 (43); 95 (37); 125 (30); 145 (96); 184 (29); 197 (57); 212 (52); 221 (22); [M]+ = 311 (100).

Compound **3h** *(4-(3 ,5 -dichlorophenylimino)-2,6-dimethoxycyclohexa-2,5-dienone)* Yield 74.0%. 1H-NMR (CDCl3, 400 MHz) δ 3.699 (s, 3H, H8), 3.874 (s, 3H, H7), 5.935 (d, 1H, *J* = 2.1 Hz, H3), 6.327 (d, 1H, *J* = 2.1 Hz, H5), 6.758 (d, 2H, *J* = 1.8 Hz, H2'), 7.167 (d, 1H, *J* = 1.8 Hz, H4'); 13C-NMR (CDCl3, 100 MHz) δ 56.375 (C8 and C7), 98.324 (C3), 111.375 (C5), 118.863 (C2'), 124.712 (C4'), 135.532 (C3' and C5'), 152.147 (C1'), 155.044 (C6), 155.938 (C2), 158.388 (C4), 176.473 (C1). mp. 170–173 ◦C. GC-MS RI(Rtx-5ms) = 2472, C14H11O3NCl2 EI-MS *m*/*z*: 109 (18); 145 (19); 212 (18); 216 (19); 231 (29); 233 (22); 246 (14); [M]<sup>+</sup> = 311 (100); [M + 2]+ = 313 (66); [M + 4]+ = 315 (13).

Compound **3i** *(4-(2 ,5 -dichlorophenylimino)-2,6-dimethoxycyclohexa-2,5-dienone)* Yield 38.3%. 1H-NMR (CDCl3, 400 MHz) δ 3.678 (s, 3H, H8), 3.893 (s, 3H, H7), 5.794 (d, 1H, *J* = 1.8 Hz, H3), 6.416 (d, 1H, *J* = 1.8 Hz, H5), 6.838 (d, 1H, *J* = 2.2 Hz, H3'), 7.094 (dd, 1H, *J* = 8.6, 2.2 Hz, H5'), 7.382 (d, 1H, *J* = 8.6 Hz, H6'); 13C-NMR (CDCl3, 100 MHz) δ 56.418 (C8 and C7), 98.759 (C3), 111.205 (C5), 121.133 (C3'), 123.120 (C1'), 125.644 (C5'), 131.130 (C6'), 133.044 (C4'), 148.282 (C2'), 155.162 (C6), 155.840 (C2), 159.208 (C4), 176.453 (C1). Mp. 198–202 ◦C. GC-MS RI(Rtx-5ms) = 2449, C14H11O3NCl2 EI-MS *m*/*z*: 190 (24); 212 (25); 231 (29); 233 (79); 261 (25); 276 (92); 278 (29); [M]<sup>+</sup> = 311 (100); [M + 2]<sup>+</sup> = 313 (73); [M + 4]+ = 315 (15).

Compound **3j** *(4-(2 -chlorophenylimino)-2,6-dimethoxycyclohexa-2,5-dienone)* Yield 44.9%. 1H-NMR (CDCl3, 400 MHz) δ 3.637 (s, 3H, H8), 3.887 (s, 3H, H7), 5.862 (s, 1H, H3), 6.460 (s, 1H, H5), 6.797 (d, 1H, *J* = 7.7 Hz, H6'), 7.119 (t, 1H, *J* = 7.6 Hz, H5'), 7.274 (t, 1H, *J* = 7.6 Hz, H4'), 7.458 (d, 1H, *J* = 8.0 Hz, H3'); 13C-NMR (CDCl3, 100 MHz) δ 56.158 (C8), 56.332 (C7), 99.002 (C3), 111.548 (C5), 121.317 (C6'), 124.984 (C1'), 125.949 (C5'), 127.326 (C4'), 130.277 (C3'), 147.388 (C2'), 154.971 (C6), 155.618 (C2), 158.576 (C4), 176.616 (C1). mp 143–146 ◦C. GC-MS RI(Rtx-5ms) = 2449, C14H12O3NCl EI-MS *m*/*z*: 150 (17); 170 (16); 178 (21); 197 (25); 199 (54); 214 (14); 242 (54); [M]<sup>+</sup> = 277 (100); [M + 1]<sup>+</sup> = 278 (16); [M + 2]+ = 279 (36).
