10.1002/ejoc.202100872
European Journal of Organic Chemistry
FULL PAPER
(d, J = 11.4 Hz, 1H), 8.64 (d, J = 11.4 Hz, 1H), 8.44 (s, 1H), 8.29 (d, J =
2.0 Hz, 1H), 7.47 – 7.45 (m, 2H), 7.18 – 7.132 (m, 4H), 7.03 – 7.01 (m,
2H), 2.89 – 2.82 (m, 2H), 1.23 – 1.19 (m, 12H); 13C NMR (150 MHz,
CDCl3) δ 163.1, 159.5, 145.9, 145.2, 134.6, 134.3, 127.4, 126.7, 120.2,
118.9, 33.4, 33.3, 23.8, 23.8; IR (ATR) 2926, 1601, 1499, 1344, 1091, 801,
739 cm-1.
CDCl3) δ 8.53 (s, 1H), 7.42 (d, J = 6.2 Hz, 1H), 6.46 (s, 1H), 6.31 (dd, J =
6.3, 1.5 Hz, 1H), 2.13 (d, J = 1.0 Hz, 3H); 13C NMR (150 MHz, CDCl3) δ
169.8, 156.1, 153.6, 137.1, 113.7, 111.7, 21.5; IR (ATR) 2939, 1598, 1488,
1262, 1153, 1044, 873, 777 cm-1.
N-Benzylformamide (2k):[53b] The title compound was prepared according
to the general procedure. The product was obtained as a brown liquid.
Yield: 95% (128 mg). 1H NMR (600 MHz, CDCl3) δ 7.94 (d, J = 1.8 Hz, 1H),
7.23 – 7.07 (m, 6H), 4.22 (d, J = 6.0 Hz, 2H); 13C NMR (150 MHz, CDCl3)
δ 164.7, 161.3, 137.4, 137.4, 128.5, 128.3, 127.5, 127.2, 127.1, 126.6,
45.3, 41.6; IR (ATR) 2890, 1640, 1528, 1448, 1390, 1230, 1080, 1042, 726,
701 cm-1.
N-(4-Methoxyphenyl)formamide (2d):[53a] The title compound was
prepared according to the general procedure. The product was obtained
as a brown liquid. Yield: 97% (146 mg). 1H NMR (600 MHz, CDCl3) δ 8.56
(d, J = 11.5 Hz, 1H), 8.48 (d, J = 11.4 Hz, 1H), 8.25 (d, J = 2.0 Hz, 1H),
7.94 (s, 1H), 7.42 – 7.40 (m, 2H), 7.01 – 6.99 (m, 2H), 6.85 – 6.83 (m, 2H),
6.81 – 6.80 (m, 2H), 3.76 (s, 3H), 3.74 (s, 3H); 13C NMR (150 MHz, CDCl3)
δ 163.4, 159.3, 157.5, 156.6, 130.0, 129.6, 121.8, 121.4, 114.8, 114.1,
55.5, 55.4; IR (ATR) 2921, 1605, 1506, 1452, 1347, 1211, 794, 747 cm-1.
N-Phenethylformamide (2l):[53e] The title compound was prepared
according to the general procedure. The product was obtained as a brown
liquid. Yield: 97% (145 mg). 1H NMR (600 MHz, CDCl3) δ 7.89 (s, 1H), 7.21
– 7.03 (m, 6H), 6.58 (s, 1H), 3.49 – 3.35 (m, 2H), 2.69 (td, J = 7.3, 2.4 Hz,
2H); 13C NMR (150 MHz, CDCl3) δ 164.6, 163.1, 161.4, 138.3, 137.4,
128.5, 128.4, 128.4, 128.3, 128.3, 126.5, 126.2, 43.0, 39.0, 37.2, 35.1; IR
(ATR) 2930, 1598, 1501, 1348, 1258, 1217, 801, 772, 740 cm-1.
N-(4-Fluorophenyl)formamide (2e):[53c] The title compound was
prepared according to the general procedure. The product was obtained
as a brown liquid. Yield: 99% (138 mg). 1H NMR (600 MHz, CDCl3) δ 8.63
(d, J = 10.7 Hz, 1H), 8.34 (d, J = 1.8 Hz, 1H), 7.71 (s, 1H), 7.47 (d, J = 8.6
Hz, 2H), 7.30 – 7.25 (m, 3H), 7.02 (d, J = 8.5 Hz, 1H); 13C NMR (150 MHz,
CDCl3) δ 162.5, 159.1, 135.3, 135.2, 130.7, 129.8, 129.7, 129.0, 121.2,
120.0; IR (ATR) 2933, 1602, 1507, 1247, 1032, 747 cm-1.
N-(1-Phenylethyl)formamide (2m):[54b] The title compound was prepared
according to the general procedure. The product was obtained as a brown
liquid. Yield: 96% (143 mg). 1H NMR (600 MHz, CDCl3) δ 7.93 (d, J = 1.7
Hz, 1H), 7.25 – 7.10 (m, 6H), 6.87 (s, 1H), 5.04 – 4.99 (m, 1H), 1.35 (dd,
J = 7.1, 1.1 Hz, 3H); 13C NMR (150 MHz, CDCl3) δ 164.3, 160.5, 142.6,
142.6, 128.6, 128.4, 127.4, 127.1, 127.1, 125.8, 125.8, 125.5, 51.7, 47.4,
23.2, 21.6, 21.6; IR (ATR) 2938, 1589, 1507, 1365, 1218, 763, 744 cm-1.
N-(4-Chlorophenyl)formamide (2f):[53a] The title compound was
prepared according to the general procedure. The product was obtained
as a brown liquid. Yield: 98% (152 mg). 1H NMR (600 MHz, CDCl3) δ 8.85
(d, J = 11.1 Hz, 1H), 8.65 (d, J = 11.2 Hz, 1H), 8.35 (d, J = 1.8 Hz, 1H),
7.96 (s, 1H), 7.49 – 7.47 (m, 2H), 7.31 – 7.25 (m, 3H), 7.04 – 7.02 (m, 1H);
13C NMR (150 MHz, CDCl3) δ 162.6, 159.2, 135.3, 135.2, 130.6, 129.8,
129.7, 129.0, 121.2, 119.9; IR (ATR) 2930, 1603, 1508, 1347, 1096, 806,
742 cm-1.
N-(Furan-2-ylmethyl)formamide (2n):[54b] The title compound was
prepared according to the general procedure. The product was obtained
as a brown solid, mp 152-154 oC. Yield: 94% (117 mg). 1H NMR (600 MHz,
CDCl3) δ 8.12 (s, 1H), 7.30 (d, J = 2.0 Hz, 1H), 6.72 (s, 1H), 6.30 – 6.21
(m, 1H), 6.18 (d, J = 3.3 Hz, 1H), 4.39 (d, J = 5.6 Hz, 2H); 13C NMR (150
MHz, CDCl3) δ 164.6, 161.1, 150.6, 150.6, 142.6, 142.1, 110.3, 110.3,
107.4, 107.3, 38.7, 34.8; IR (ATR) 1370, 1214, 791, 740 cm-1.
Methyl 4-formamidobenzoate (2g):[53d] The title compound was prepared
according to the general procedure. The product was obtained as a brown
liquid. Yield: 96% (172 mg). 1H NMR (600 MHz, CDCl3) δ 8.89 – 8.80 (m,
2H), 8.40 (d, J = 1.8 Hz, 1H), 8.06 (s, 1H), 7.99 (dd, J = 17.3, 8.4 Hz, 4H),
7.64 – 7.58 (m, 2H), 7.13 (d, J = 8.4 Hz, 2H), 3.88 (d, J = 7.7 Hz, 5H); 13
C
N-Isobutylformamide (2o):[54c] The title compound was prepared
according to the general procedure. The product was obtained as a brown
solid, mp 146-148oC. Yield: 95% (96 mg). 1H NMR (600 MHz, CDCl3) δ
8.05 (d, J = 2.2 Hz, 1H), 6.67 (s, 1H), 2.99 (t, J = 6.5 Hz, 2H), 1.70 – 1.67
(m, 1H), 0.82 – 0.80 (m, 8H); 13C NMR (150 MHz, CDCl3) δ 165.0, 161.5,
49.2, 45.2, 29.3, 28.1, 19.8, 19.8, 19.3; IR (ATR) 2800, 1453, 1376, 782,
746, 698 cm-1.
NMR (150 MHz, CDCl3) δ 166.5, 166.3, 162.1, 159.2, 141.0, 140.9, 131.4,
130.8, 126.4, 126.0, 119.1, 117.1, 52.1, 52.0; IR (ATR) 2927, 1599, 1504,
1347, 1255, 1215, 796, 741cm-1.
N-(Naphthalen-2-yl)formamide (2h):[53e] The title compound was
prepared according to the general procedure. The product was obtained
as a brown solid, mp 84-86 oC. Yield: 96% (164 mg). 1H NMR (600 MHz,
CDCl3) δ 9.23 (d, J = 10.5 Hz, 1H), 8.63 (d, J = 10.7 Hz, 1H), 8.04 (d, J =
8.2 Hz, 1H), 7.97 – 7.81 (m, 2H), 7.75 (d, J = 8.3 Hz, 1H), 7.57 – 7.51 (m,
2H), 7.47 – 7.39 (m, 2H), 7.27 (d, J = 7.3 Hz, 1H); 13C NMR (150 MHz,
CDCl3) δ 164.4, 159.9, 134.2, 133.9, 132.3, 131.1, 128.6, 128.3, 127.7,
126.8, 126.8, 126.6, 126.3, 126.0, 125.9, 125.5, 125.3, 121.4, 120.8, 120.5,
118.7; IR (ATR) 1675, 1630, 1441, 1350, 1246, 929, 793 cm-1.
N-Hexylformamide (2p):[54d] The title compound was prepared according
to the general procedure. The product was obtained as a brown liquid.
Yield: 95% (123 mg). 1H NMR (600 MHz, CDCl3) δ 8.11 (d, J = 1.7 Hz, 1H),
5.95 (s, 1H), 3.24 (q, J = 6.8 Hz, 2H), 1.53 – 1.45 (m, 3H), 1.30 – 1.21 (m,
8H), 0.87 – 0.82 (m, 4H); 13C NMR (150 MHz, CDCl3) δ 164.6, 161.2, 41.8,
38.1, 31.3, 31.2, 31.0, 29.3, 26.4, 25.9, 22.4, 22.4, 13.9, 13.8; IR (ATR)
2799, 1451, 1366, 778, 744, 700 cm-1.
N-(Pyridin-2-yl)formimidic acid (2i):[53e] The title compound was
prepared according to the general procedure. The product was obtained
as a brown liquid. Yield: 96% (117 mg). 1H NMR (600 MHz, CDCl3) δ 8.51
(s, 1H), 7.67 (dd, J = 6.1, 1.7 Hz, 1H), 7.53 – 7.50 (m, 1H), 6.71 (d, J = 8.7
Hz, 1H), 6.57 (t, J = 6.4 Hz, 1H); 13C NMR (150 MHz, CDCl3) δ 169.2,
156.4, 141.2, 138.5, 112.2, 111.91; IR (ATR) 3019, 2917, 1656, 1446,
1370, 1220, 1096, 804, 750 cm-1.
N-Isopropylformamide (2q):[55a] The title compound was prepared
according to the general procedure. The product was obtained as a brown
liquid. Yield: 96% (84 mg). 1H NMR (600 MHz, CDCl3) δ 7.93 (s, 1H), 6.56
(s, 1H), 4.03 – 3.97 (m, 1H), 1.12 (d, J = 6.6 Hz, 1H), 1.06 (d, J = 6.6 Hz,
6H); 13C NMR (150 MHz, CDCl3) δ 164.0, 163.2, 160.8, 44.3, 40.1, 23.8,
22.2, 22.2; IR (ATR) 2916, 2798, 1653, 1437, 1366, 1089, 849, 748, 698
cm-1.
N-(4-Methylpyridin-2-yl)formimidic acid (2j):[54a] The title compound
was prepared according to the general procedure. The product was
obtained as a brown liquid. Yield: 94% (128 mg). 1H NMR (600 MHz,
N-Cyclohexylformamide (2r):[54b] The title compound was prepared
according to the general procedure. The product was obtained as a brown
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