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HETEROCYCLES, Vol. 88, No. 1, 2014
N-(4-Methoxyphenyl)formamide (3ee).16 Purification of the crude mixture by column chromatography
(CH2Cl2:AcOEt 95:5) afforded the product as brown powder. 1H NMR (300 MHz, CDCl3), two rotamers.
! [9.13 (d, J = 11.8 Hz), 8.81 (br. s), 1H], 8.53 (d, J = 11.8 Hz), 8.26 (d, J = 2.0 Hz), 1H], (7.47, 7.04,
13
6.85, 3m, 4H), (3.77, 3.74, 2s, 3H). C NMR (75 MHz, CDCl3), two rotamers. ! 163.6, 159.9, 157.5,
156.6, 130.3, 129.9, 122.1, 121.4, 116.9, 114.9, 114.2, 55.5, 55.4.
N-Cyclohexylformamide (3ei).16 Purification of the crude mixture by column chromatography
1
(CH2Cl2:AcOEt 9:1) afforded the product as yellow solid. H NMR (300 MHz, CDCl3) ! 8.12 (s, 1H),
8.06 (s, 1H), 6.20 (broad s, 1H), 5.98 (broad s, 1H), 3.89-3.75 (m, 1H) and 3.35-3.22 (m, 1H), 1.94-1.08
(m, 10H). 13C NMR (75 MHz, CDCl3) ! 163.8, 160.5, 51.2, 47.2, 34.8, 33.1, 25.5, 25.1, 24.9.
28
N-p-Tolylformamide (3ej).
Purification of the crude mixture by column chromatography
1
(CH2Cl2:AcOEt 95:5) afforded the product as yellow solid. H NMR (300 MHz, CDCl3), two rotamers
(1:1) ! 8.97, 8.18 (2 br. s, 1H), [8.66 (d, J = 12.0 Hz), 8.33 (s), 1H], 7.48 (d, J = 8.5.0 Hz, 1H), 7.16-6.38
13
(m, 2H), 7.02 (d, J = 8.5.0 Hz, 1H), 2.37, 2.33 (2s, 3H). C NMR (75 MHz, CDCl3), two rotamers !
163.3, 159.5, 135.0, 134.8, 130.3, 129.7, 120.4, 119.3, 20.9, 20.8.
N-Phenethylnicotinamide (3fh). 29 Purification of the crude mixture by column chromatography
(CH2Cl2:AcOEt 9:1) afforded the product as a white powder. 1H NMR (300 MHz, CDCl3) ! 8.88 (s, 1H),
13
8.58 (s, 1H), 8.05 (m, 1H), 7.71 (m, 7H), 3.69 (dd, J = 12.8, 6.9 Hz, 2H), 2.92 (t, J = 6.9 Hz, 2H). C
NMR (75 MHz, CDCl3) ! 166.0, 151.8, 147.9, 138.9, 135.4, 129.1, 126.6, 123.6, 41.6, 35.8.
30
N-Hexylnicotinamide (3fj).
Purification of the crude mixture by column chromatography
(CH2Cl2:AcOEt 9:1) afforded the product as a white powder. 1H NMR (300 MHz, CDCl3) ! 8.94 (m, 1H),
8.52 (br. s, 1H), 8.05 (m, 1H), 7.76 (m, 1H), 7.23 (m, 1H), 3.33 (dd, J = 13.3, 6.7 Hz, 2H), 1.51 (m, 2H),
13
1.19 (m, 6H), 0.76 (t, J = 6.6 Hz, 3H). C NMR (75 MHz, CDCl3) ! 165.8, 151.9, 148.3, 135.4, 130.9,
123.6, 40.3, 31.4, 29.4, 26.7, 22.5, 14.0.
N-Phenethylisonicotinamide (3gh). Purification of the crude mixture by column chromatography
(CH2Cl2:AcOEt 9:1) afforded the product as a white powder. 1H NMR (300 MHz, CDCl3) ! 8.67 (m, 2H),
7.53 (m, 2H), 7.29 (m, 5H), 6.63 (br. s, 1H), 3.75 (dd, J = 12.8, 6.9 Hz, 2H), 2.95 (t, J = 6.9 Hz, 2H). 13C
NMR (75 MHz, CDCl3) ! 165.5, 150.6, 138.5, 128.8, 121.3, 41.5, 35.3. HRMS (ESI+) m/z [M+H]+ calcd
for C14H15N2O 227.2817, found 227.2830.
N-Hexylisonicotinamide (3gj). 31 Purification of the crude mixture by column chromatography
(CH2Cl2:AcOEt 9:1) afforded the product as a white powder. 1H NMR (300 MHz, CDCl3) ! 8.61 (m, 2H),
7.62 (m, 2H), 7.29 (br. s, 1H), 3.38 (dd, J = 13.3, 6.7 Hz, 2H), 1.55 (m, 2H), 1.26 (m, 6H), 0.83 (t, J = 6.6
Hz, 3H). 13C NMR (75 MHz, CDCl3) ! 165.6, 150.4, 142.1, 121.4, 40.7, 31.8, 29.6, 27.0, 22.6, 14.1.
N1,N4-Dibenzylsuccinamide (3ha).32 Purification of the crude mixture by washing with CH2Cl2 afforded
the product as a white powder. 1H NMR (300 MHz, CDCl3) ! 8.35 (t, J = 5.2 Hz, 2H), 7.27 (m, 10H),