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Organic & Biomolecular Chemistry
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CDCl3) δ 161.4, 158.7, 148.0, 147.1, 126.9, 126.3, 125.1, 124.2, N-(4-chlorophenyl)formamide (2t):32 White solid (26.9 mg,
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121.0, 120.9, 120.5, 116.4, 112.2, 111.0, 64.3, 64.2, 14.9, 14.8.
DOI: 10.1039/C8OB00490K
N-(2-methoxyphenyl)formamide (2k):25 White solid (26.7 mg, 10.12 (m, 1H), 8.79 (d, J = 10.9 Hz, 1H), 8.28 (d, J = 1.7 Hz, 1H),
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90%); mp 80-82 C; H NMR (500 MHz, CDCl3) δ 8.73 (d, J = 7.61 (d, J = 8.8 Hz, 1.56H), 7.44 – 7.31 (m, 2H), 7.22 (d, J = 8.8
11.6 Hz, 0.57H), 8.45 (d, J = 1.5 Hz, 1H), 8.36 (dd, J = 8.0, 1.4 Hz, Hz, 0.43H). 13C NMR (125 MHz, DMSO) δ 162.5, 159.7, 137.1,
1H), 7.89 (s, 1H), 7.76 (s, 0.60H), 7.19 (dd, J = 7.8, 1.1 Hz, 129.2, 128.7, 127.1, 120.7, 118.9.
0.57H), 7.13 (td, J = 7.9, 1.4 Hz, 0.60H), 7.07 (td, J = 7.9, 1.6 Hz, N-(4-fluoropheny)formamide (2u):26 White solid (26.4 mg,
1H), 7.00 – 6.85 (m, 4H), 3.87 (d, J = 9.4 Hz, 6H). 13C NMR (125 93%); mp 62-64 C; H NMR (500 MHz, CDCl3) δ 8.58 (d, J =
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MHz, CDCl3) δ 161.5, 158.8, 148.8, 147.8, 126.8, 126.2, 125.2, 11.0 Hz, 1H), 8.55 (brs, 1H), 8.35 (s, 1H), 7.66 (brs, 1H), 7.56 –
124.3, 121.09 (d), 120.5, 116.7, 111.3, 110.1, 55.7.
7.46 (m, 2H), 7.17 – 6.94 (m, 6H). 13C NMR (125 MHz, CDCl3) δ
N-(2-hydroxyphenyl)formamide (2l):26 Yellow solid (11.1 mg, 162.9, 159.0, 132.8 (dd, J = 17.8, 2.7 Hz), 121.9 (d, J = 7.9 Hz),
40%); mp 166-168 oC; 1H NMR (500 MHz, DMSO) δ 9.95 (s, 1H), 121.2 (d, J = 8.2 Hz), 116.7, 116.5, 115.9, 115.7.
9.57 (s, 1H), 8.27 (d, J = 2.0 Hz, 1H), 8.02 (dd, J = 8.0, 1.4 Hz, N-(2-fluoropheny)formamide (2v): Yellow oil (18.0 mg, 64%);
1H), 7.15 – 6.70 (m, 4H). 13C NMR (125 MHz, DMSO) δ 160.0, 1H NMR (500 MHz, CDCl3) δ 8.62 (d, J = 11.3 Hz, 1H), 8.40 (s,
146.7, 126.0, 124.1, 120.8, 118.9, 115.1.
1H), 8.26 (t, J = 7.9 Hz, 1H), 7.71 (brs, 1H), 7.53 (brs, 1H), 7.24 –
N-(4-bromophenyl)formamide (2m):26 White solid (28.8 mg, 6.92 (m, 3H). 13C NMR (125 MHz, CDCl3) δ 161.9, 158.8, 153.2,
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73%); mp 113-115 C; 1H NMR (500 MHz, DMSO) δ 10.56 – 151.3, 126.0 (d), 125.4 (d), 124.9 (d), 124.7 (d), 122.2, 119.6,
10.15 (m, 1H), 8.79 (d, J = 10.9 Hz, 1H), 8.29 (d, J = 1.7 Hz, 1H), 116.45 (d), 114.92 (d).
7.60 – 7.52 (m, 1.58H), 7.52 – 7.45 (m, 2H), 7.16 (d, J = 8.7 Hz, N-(4-((trifluoromethyl)thio)phenyl)formamide (2w): White
0.43H). 13C NMR (125 MHz, DMSO) δ 162.5, 159.7, 137.8, solid (28.4 mg, 65%); mp 105-107 oC; 1H NMR (500 MHz, CDCl3)
137.5, 132.1, 131.6, 121.0, 119.3, 115.1.
δ 8.80 (d, J = 10.9 Hz, 1H), 8.73 (s, 1H), 8.43 (s, 1H), 7.74 – 7.52
N-(2-bromophenyl)formamide (2n):26 Pale yellow solid (16.2 (m, 7H), 7.16 (d, J = 8.0 Hz, 1H). 13C NMR (125 MHz, CDCl3) δ
mg, 41%); mp 83-85 oC; 1H NMR (500 MHz, CDCl3) δ 8.71 (d, J = 162.1, 159.1, 139.4, 138.2, 137.5, 120.5, 118.7.
11.1 Hz, 1H), 8.50 (s, 1H), 8.40 (d, J = 8.2 Hz, 1H), 7.67 (brs, 2H), N-(naphthalene-2-yl)formamide (2x): Yellow solid (24.7 mg,
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7.61 (d, J = 8.0 Hz, 1H), 7.56 (d, J = 8.0 Hz, 1H), 7.33 (t, J = 7.8 73%); mp 121-123 C; H NMR (500 MHz, DMSO) δ 10.49 –
Hz, 2H), 7.27 (d, J = 7.3 Hz, 1H), 7.08 (t, J = 7.7 Hz, 1H), 7.02 (t, J 10.32 (m, 2H), 8.97 (d, J = 10.9 Hz, 1H), 8.39 (d, J = 1.8 Hz, 1H),
= 7.7 Hz, 1H). 13C NMR (125 MHz, CDCl3) δ 161.4, 158.7, 135.0 8.33 (d, J = 1.7 Hz, 1H), 7.95 – 7.33 (m, 13H). 13C NMR (125
(d, J = 32.6 Hz), 133.5, 132.4, 128.7, 128.5, 126.4, 125.6, 122.3, MHz, DMSO) δ 162.6, 159.8, 135.8, 133.4, 129.92 (d), 129.2,
118.9, 114.4, 113.0.
128.5, 127.5 (d), 127.3, 126.9, 126.7, 126.5, 124.6 (d), 119.7,
N-(3-bromophenyl)formamide (2o):26 Yellow solid (30.0 mg, 118.5, 115.4, 112.8.
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76%); mp 50-52 C; H NMR (500 MHz, CDCl3) δ 8.83 (d, J = N-(naphthalene-1-yl)formamide (2y): White solid (26.3 mg,
10.0 Hz, 1H), 8.62 (d, J = 11.2 Hz, 1H), 8.29 (d, J = 1.6 Hz, 1H), 76%); mp 130-132 oC; 1H NMR (500 MHz, DMSO) δ 10.54 (d, J =
7.85 (brs, 1H), 7.73 (t, J = 1.9 Hz, 1H), 7.38 (dd, J = 8.1, 1.0 Hz, 10.3 Hz, 1H), 10.35 (s, 1H), 8.61 (d, J = 10.5 Hz, 1H), 8.51 (d, J =
1H), 7.30 – 7.05 (m, 5H), 6.97 (dd, J = 8.0, 1.4 Hz, 1H). 13C NMR 1.8 Hz, 1H), 8.15 (dd, J = 10.1, 6.1 Hz, 2H), 8.03 (d, J = 7.5 Hz,
(125 MHz, CDCl3) δ 162.6, 159.3, 138.1, 131.1, 130.4, 128.3, 1H), 7.99 – 7.91 (m, 2H), 7.80 (d, J = 8.2 Hz, 1H), 7.75 (d, J = 8.2
127.9, 123.4, 123.0, 122.7, 121.7, 118.5, 117.2.
Hz, 1H), 7.64 – 7.45 (m, 6H), 7.42 (d, J = 7.3 Hz, 1H). 13C NMR
N-(4-iodophenyl)formamide (2p):30 White solid (27.1 mg, (125 MHz, DMSO) δ 164.0, 160.3, 133.8, 133.6, 132.6, 128.3,
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55%); mp 102-104 C; H NMR (500 MHz, CDCl3) δ 8.66 (d, J = 128.1, 126.5, 126.2, 126.11, 126.06, 126.0, 125.8, 125.6, 125.5,
11.1 Hz, 1H), 8.49 (s, 1H), 8.36 – 8.25 (m, 1H), 7.91 – 7.75 (m, 124.8, 122.5, 121.8, 119.3, 118.2.
2H), 7.49 (brs, 2H), 7.36 (t, J = 7.8 Hz, 2H), 7.22 (d, J = 7.9 Hz, N-(thiophen-2-yl)formamide (2z): Yellow solid (16.5 mg, 65%);
1H), 6.91 (ddd, J = 15.3, 11.5, 4.4 Hz, 2H). 13C NMR (125 MHz, mp 60-62 oC; 1H NMR (500 MHz, CDCl3) δ 8.78 (s, 1H), 8.41 (d, J
CDCl3) δ 161.8, 158.8, 140.0, 139.0, 137.8, 137.3, 129.7, 129.4, = 11.1 Hz, 1H), 8.35 (d, J = 1.0 Hz, 1H), 7.94 (s, 1H), 7.09 – 6.66
127.0, 126.4, 122.3, 119.3, 90.7, 89.2.
(m, 6H). 13C NMR (125 MHz, CDCl3) δ 163.7, 157.5, 138.1, 137.2,
N-(2-iodophenyl)formamide (2q):31 White solid (19.8 mg, 126.2, 124.2, 121.4, 119.9, 118.7, 113.4.
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40%); mp 105-107 C; H NMR (500 MHz, CDCl3) δ 8.68 (d, J = N-(furan-2-yl)formamide (2a’): White solid (12.1 mg, 54%); mp
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11.3 Hz, 1H), 8.59 (brs, 1H), 8.38 (d, J = 1.5 Hz, 1H), 7.64 (dd, J 120-122 C; H NMR (500 MHz, CDCl3) δ 7.48 (s, 1H), 7.17 (d, J
= 15.6, 8.7 Hz, 2H), 7.33 (d, J = 8.7 Hz, 1H), 6.87 (d, J = 8.6 Hz, = 3.1 Hz, 1H), 6.52 (t, J = 1.5 Hz, 1H), 6.26 (brs, 1H), 5.59 (brs,
1H). 13C NMR (125 MHz, CDCl3) δ 162.3, 159.0, 138.7, 138.1, 1H). 13C NMR (125 MHz, CDCl3) δ 144.4, 115.3, 112.3.
121.8, 120.5.
N-(quinolin-4-yl)formamide(2b’): Yellow oil; 1H NMR (400 MHz,
N-(2-chlorophenyl)formamide (2r):26 White solid (13.6 mg, DMSO) δ 8.99 (d, J = 4.3 Hz, 1H), 8.25 (d, J = 8.5 Hz, 2H), 8.10 (d,
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44%); mp 80-82 C; H NMR (500 MHz, CDCl3) δ 8.73 (d, J = J = 8.4 Hz, 1H), 7.93 (s, 1H), 7.86 – 7.79 (m, 1H), 7.70 (dd, J =
11.2 Hz, 1H), 8.51 (s, 1H), 8.41 (d, J = 8.2 Hz, 1H), 7.71 (s, 1H), 11.2, 4.0 Hz, 1H), 7.59 (d, J = 4.3 Hz, 1H). 13C NMR (125 MHz,
7.48 – 7.03 (m, 3H). 13C NMR (125 MHz, CDCl3) δ 161.4, 158.7, DMSO) δ 169.1 (s), 150.7 (s), 148.4 (s), 142.6 (s), 130.2 (s),
133.8 (d), 130.3, 129.1, 127.9 (d), 125.9, 125.1, 124.2, 122.5, 129.8 (s), 127.7 (s), 126.0 (s), 124.5 (s), 119.3 (s).
122.0, 118.6.
N-adamantylformamide (2c’):33 White solid (22.5 mg, 62%);
N-(3-chlorophenyl)formamide (2s):26,32 White solid (21.5 mg, mp 118-120 oC; 1H NMR (500 MHz, CDCl3) δ 8.20 (d, J = 12.4 Hz,
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69%); mp 48-50 C; H NMR (500 MHz, CDCl3) δ 8.87 (brs, 1H), 1H), 7.96 (d, J = 1.8 Hz, 1H), 6.05 (brs, 1H), 5.16 (brs, 1H), 2.18
8.71 (d, J = 11.2 Hz, 1H), 8.37 (s, 1H), 7.95 (brs, 1H), 7.67 (s, 1H), – 1.40 (m, 30H). 13C NMR (125 MHz, CDCl3) δ 162.2, 160.2, 52.2,
7.40 (d, J = 8.0 Hz, 1H), 7.26 (dt, J = 20.7, 8.1 Hz, 2H), 7.19 – 50.7, 44.2, 41.9, 36.2, 35.9, 29.4, 29.3.
7.07 (m, 3H), 7.03 – 6.97 (m, 1H). 13C NMR (125 MHz, CDCl3) δ N-benzylformamide (2d’):25 White solid (22.2 mg, 83%); mp
162.6, 159.3, 138.0 (d), 135.5, 134.7, 130.8, 130.1, 125.3, 53-55 oC; 1H NMR (500 MHz, CDCl3) δ 8.19 (s, 0.86H), 8.10 (d, J
124.9, 120.2, 118.8, 118.0, 116.7.
= 11.9 Hz, 0.16H), 7.41 – 7.19 (m, 5H), 6.33 (brs, 1H), 4.43 (d, J
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