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6.4.1. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(3-(6-bro-
mopyridin-2-yl)-2-cyanoacrylamide) (8a)
J = 7.7, 2H), 7.07 (d, J = 8.9, 4H), 4.41 (d, J = 5.9, 4H), 4.06 (t,
J = 6.5, 4H), 1.85–1.64 (m, 4H), 1.42 (s, 4H), 1.37–1.18 (m, 8H),
0.88 (t, J = 7.1, 6H).; 13C NMR (126 MHz, DMSO) d 162.6, 161.9,
150.7, 139.6, 133.0, 128.7, 126.4, 126.3, 124.6, 117.4, 115.6,
102.7, 68.4, 43.4, 31.4, 28.9, 25.5, 22.5, 14.3.; HRMS (C40H46N4O4)
calcd 646.3592 found 647.3599 [M+H].
N,N0-(1,3-phenylenebis(methylene))bis(2-cyanoacetamide)
(2.7 g, 1 mM), 6-bromo-2-pyridine carboxaldehyde (3.8 g, 2 mM),
and 300 lL of piperidine in 50 mL of acetonitrile were heated at
60 °C for 16 h. Cooling and filtering yielded 4 g of a white solid
(67% yield). 1H NMR (500 MHz, DMSO) d 9.13 (s, 2H), 8.11 (s,
2H), 7.92 (t, J = 7.7, 2H), 7.86 (d, J = 7.2, 2H), 7.79 (d, J = 7.8, 2H),
7.32 (d, J = 7.4, 1H), 7.29 (s, 1H), 7.23 (d, J = 7.6, 2H), 4.44 (d,
J = 5.9, 4H).; 13C NMR (126 MHz, DMSO) d 161.2, 151.4, 147.1,
141.6, 141.1, 139.3, 131.0, 128.9, 127.0, 126.7, 126.5, 115.4,
110.7, 43.6.; HRMS (C26H18Br2N6O2) calcd 604.9931 found
604.9947 [M+H].
6.4.8. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(3-hydroxy-4-nitrophenyl)acrylamide) (8h)
1H NMR (DMSO-d6) d 9.17 (m, 2H), 8.16 (s, 2H), 7.96 (m, 2H),
7.60 (s, 2H), 7.42 (m, 2H), 7.33 (m, 1H), 7.30 (s, 1H), 7.20 (m,2H),
4.37 (m, 4H).; 13C NMR (150 MHz, CDCl3) d 160.5, 148.7, 138.8,
138.7, 137.4, 126.1, 125.8, 120.2, 115.5, 109.3, 43.1.; HRMS
(C28H20N6O8) calcd 569.1415 found 569.1413 [M+H].
6.4.2. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(4-(piperidin-1-yl)phenyl)acrylamide) (8b)
6.4.9. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(3,4-dimethoxyphenyl)acrylamide) (8i)
1H NMR (500 MHz, DMSO) d 8.72 (s, 2H), 7.98 (s, 2H), 7.82 (d,
J = 9.0, 4H), 7.29 (s, 1H), 7.25 (s, 1H), 7.19 (d, J = 7.5, 2H), 6.99 (d,
J = 9.1, 4H), 4.40 (s, 4H), 3.46 (s, 7H), 1.57 (s, 13H).; 13C NMR
(126 MHz, DMSO) d 162.65, 153.6, 150.7, 139.8, 133.2, 128.7,
126.6, 126.4, 120.1, 118.4, 113.8, 98.0, 47.9, 43.4, 25.4, 24.4.; HRMS
(C38H40N6O2) calcd 613.3286 found 613.3297 [M+H].
1H NMR (500 MHz, DMSO) d 9.28 (s, 2H), 8.13 (s, 2H), 7.48 (d,
J = 8.2, 2H), 7.39 (d, J = 8.3, 2H), 7.35 (s, 1H), 7.30 (s, 1H), 7.24 (d,
J = 7.6, 2H), 4.44 (d, J = 5.9, 5H), 3.79 (s, 6H);2.27 (s, 3H) 2.26 (s,
3H).; 13C NMR (150 MHz, CDCl3) d 161.4, 152.5, 150.6, 148.6,
139.1, 128.2, 125.9, 124.4, 117.0, 112.2, 111.7, 102.3, 55.7, 55.4,
43.0.; HRMS (C32H30N4O6) calcd 567.2238 found 567.2236 [M+H].
6.4.3. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(3,4-dichlorophenyl)acrylamide) (8c)
6.4.10. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(1H-imidazol-5-yl)acrylamide) (8k)
1H NMR (500 MHz, DMSO) d 9.10 (t, J = 5.9, 2H), 8.17 (s, 2H),
8.10 (d, J = 2.0, 2H), 7.88 (d, J = 2.0, 1H), 7.86 (d, J = 2.0, 1H), 7.81
(s, 1H), 7.79 (s, 1H), 7.35–7.29 (m, 1H), 7.27–7.17 (m, 3H), 4.43
(d, J = 5.9, 4H).; 13C NMR (126 MHz, DMSO) d 161.0, 148.6, 139.3,
135.1, 132.8, 132.4, 132.0, 131.8, 130.0, 128.8, 126.5, 126.2,
116.2, 108.6, 43.5.; HRMS (C25H16Cl4N6O2) calcd 585.0162 found
585.0191 [M+H].
1H NMR (500 MHz, DMSO) d 8.79 (s, 2H), 8.08 (s, 2H), 7.96 (d,
J = 9.4, 4H), 7.30 (s, 1H), 7.25 (s, 1H), 7.20 (s, 2H), 4.40 (d, J = 5.9,
4H).; 13C NMR (126 MHz, DMSO) d 162.2, 143.6, 139.7, 138.8,
128.7, 126.8, 126.4, 117.3, 100.5, 43.5.; HRMS (C28H22N8O2) calcd
427.1625 found 427.1640 [M+H].
6.4.11. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(3-([2,20-
bithiophen]-5-yl)-2-cyanoacrylamide) (8l)
6.4.4. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(6-methoxypyridin-2-yl)acrylamide) (8d)
1H NMR (500 MHz, DMSO) d 8.92 (t, J = 5.9, 2H), 8.36 (s, 2H),
7.80 (d, J = 4.2, 2H), 7.68 (dd, J = 5.1, 1.0, 2H), 7.52 (dd, J = 3.6, 1.0,
2H), 7.46 (d, J = 4.0, 2H), 7.34–7.27 (m, 1H), 7.27–7.18 (m, 3H),
7.16 (dd, J = 5.0, 3.7, 2H), 4.41 (d, J = 5.9, 4H).; 13C NMR
(126 MHz, DMSO) d 161.4, 145.0, 143.8, 140.3, 139.5, 135.5,
134.5, 129.4, 128.7, 128.7, 127.1, 126.4, 126.3, 125.2, 117.1,
100.9, 43.5.; HRMS (C32H22N4O2S4) calcd 623.0698 found
623.0700 [M+H].
1H NMR (500 MHz, DMSO) d 9.03 (t, J = 6.0, 2H), 8.06 (s, 2H),
7.82 (dd, J = 8.4, 7.2, 2H), 7.34 (d, J = 6.9, 2H), 7.31 (d, J = 7.4, 1H),
7.27 (s, 1H), 7.23 (d, J = 7.7, 2H), 6.99 (d, J = 8.1, 2H), 4.44 (d,
J = 5.9, 4H), 3.97 (s, 6H).; 13C NMR (126 MHz, DMSO) d 163.4,
161.6, 148.9, 147.7, 140.6, 139.4, 128.8, 126.4, 122.4, 116.5,
115.3, 108.7, 54.6, 43.6.; HRMS (C28H24N6O4) calcd 509.1932 found
509.1921 [M+H].
6.4.5. (2E,20E)-N,N0-(1,3-phenylenebis(methylene))bis(3-(6-
chloro-2-fluoro-3-methylphenyl)-2-cyanoacrylamide) (8e)
1H NMR (DMSO-d6) d 9.287 (t, 2H), 8.15 (s, 2H), 7.49 (m, 2H),
7.40 (m, 2H), 7.31 (mt, 1H), 7.25 (s, 1H), 7.25 (m, 2H), 4.45 (m,
4H), and 2.27 (s, 6H).; 13C NMR (150 MHz, CDCl3) d 159.4, 143.2,
138.7, 134.3, 128.4, 126.5, 126.3, 125.2, 124.6, 119.7, 115.5,
114.4, 43.5, 13.8.; HRMS (C30H22Cl2F2N4O2) calcd 579.1161 found
597.1155 [M+H].
6.4.12. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(4-phenylthiophen-2-yl)acrylamide) (8m)
1H NMR (500 MHz, DMSO) d 8.99 (t, J = 5.9, 2H), 8.44 (s, 2H),
8.35 (s, 2H), 8.26 (d, J = 1.2, 2H), 7.71 (d, J = 7.2, 4H), 7.45 (t,
J = 7.7, 4H), 7.30 (ddd, J = 44.1, 22.9, 7.5, 7H), 4.43 (d, J = 5.9, 4H).;
13C NMR (126 MHz, DMSO) d 161.3, 144.2, 142.5, 139.5, 136.9,
136.6, 134.1, 130.0, 129.6, 128.8, 128.4, 126.5, 126.5, 116.9,
102.3, 43.6.; HRMS (C32H26N4O2S2) calcd 611.1570 found
611.1562 [M+H].
6.4.6. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(3-(3-bro-
mo-4-hydroxyphenyl)-2-cyanoacrylamide) (8f)
6.4.13. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(1H-indol-3-yl)acrylamide)MS 525.6 (M+H) (8n)
1H NMR (500 MHz, DMSO) d 8.81 (t, J = 5.9, 2H), 8.16 (d, J = 2.1,
2H), 8.00 (s, 2H), 7.77 (dd, J = 8.7, 2.1, 2H), 7.34 – 7.27 (m, 1H), 7.25
(s, 1H), 7.20 (d, J = 7.5, 2H), 6.95 (d, J = 8.6, 2H), 4.40 (d, J = 5.8, 4H).;
13C NMR (126 MHz, DMSO) d 162.2, 161.5, 149.7, 139.6, 135.6,
132.6, 128.7, 126.7, 126.5, 126.4, 122.7, 117.8, 111.9, 100.5, 44.3,
43.5.; HRMS (C28H20Br2N4O4) calcd634.9924 found 634.9928
[M+H].
1H NMR (500 MHz, DMSO) d 8.86 (t, J = 5.9, 2H), 8.51 (s,1, 2H),
8.44 (s,1, 2H), 7.89 (d, J = 7.8, 2H), 7.64–7.15 (m, 11H), 4.44 (d,
J = 5.9, 4H).; 13C NMR (126 MHz, DMSO) d 162.7, 142.8, 139.4,
136.5, 130.5, 128.2, 127.0, 126.2, 126.4, 123.7, 122.0, 119.1,
118.8, 113.2, 110.0, 97.6, 43.4.; HRMS (C32H24N6O2) calcd
525.2034 found 525.2051 [M+H], 547.1859 [M+Na].
6.4.7. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(2-cyano-
3-(4-(hexyloxy)phenyl)acrylamide) (8g)
6.4.14. (2Z,20Z)-N,N0-(1,3-phenylenebis(methylene))bis(3-
(benzo[b]thiophen-3-yl)-2-cyanoacrylamide) (8o)
1H NMR (500 MHz, DMSO) d 8.92 (t, J = 5.9, 2H), 8.10 (s, 2H),
7.91 (d, J = 9.0, 4H), 7.35–7.28 (m, 1H), 7.25 (s, 1H), 7.21 (d,
1H NMR (500 MHz, DMSO) d 9.23 (t, J = 5.9, 2H), 8.77 (s, 2H),
8.45 (s, 2H), 8.09 (d, J = 7.5, 4H), 7.49 (dd, J = 13.7, 7.0, 4H), 7.38–