HETEROCYCLES, Vol. 87, No. 1, 2013
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Reaction time: 3 h. Yield 71%; mp 159-161 C (toluene). 1H NMR (400 MHz, DMSO-d6): δ 2.95 (3H, s,
NMe), 3.07 (3H, s, NMe), 7.57 (1H, br. s, H-5/3), 8.40 (1H, s, N=CH-NMe2), 12.86 (1H, br. s, N(1)H). 13C
NMR (100 MHz, DMSO-d6): δ 34.0 (NMe), 40.0 (NMe), 148.9 (C-5/3), 157.2 (N=CH-NMe2), 160.7
(C-3/5). Anal. Calcd for C5H9N5: C, 43.15; H, 6.52; N, 50.33. Found: C, 43.12; H, 6.57; N, 50.28.
N1,N1-Dimethyl-N2-[3(5)-phenyl-1,2,4-triazol-5(3)-yl]formamidine (7b)
Reaction time: 1.5 h. Yield 93%; mp 199-201 C (toluene). 1H NMR (400 MHz, DMSO-d6): δ 2.99 (3H, s,
NMe), 3.12 (3H, s, NMe), 7.35 (1H, t, J = 7.3 Hz, H-4′), 7.42 (2H, t, J = 7.5 Hz, H-3′ and H-5′), 7.99 (2H, d,
J = 7.5 Hz, H-2′ and H-6′), 8.41* and 8.52 (1H, s, N=CH-NMe2), 12.97 and 13.67* (1H, s, N(1)H);
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*- signals of minor tautomeric form (KT = 23.4). C NMR (100 MHz, DMSO-d6): δ 34.1 (NMe), 40.1
(NMe), 125.3 (C-3′ and C-5′), 128.2 (C-4′), 128.9 (C-2′ and C-6′), 132.3 (C-1′), 157.3 (N=CH-NMe2),
158.7 (C-5), 160.9 (C-3). Anal. Calcd for C11H13N5: C, 61.38; H, 6.09; N, 32.54. Found: C, 61.41; H, 6.12;
N, 32.46.
N1,N1-Dimethyl-N2-[3(5)-phenylamino-1,2,4-triazol-5(3)-yl]formamidine (7c)
Reaction time: 10 min. Yield 96%; mp 207-209 C (toluene). 1H NMR (400 MHz, DMSO-d6): δ 2.96 (3H,
s, NMe), 3.07 (3H, s, NMe), 6.73 (1H, t, J = 7.3 Hz, H-4′), 7.17 (2H, t, J = 7.9 Hz, H-3′ and H-5′), 7.53 (2H,
d, J = 8.6 Hz, H-2′ and H-6′), 8.34 (1H, s, N=CH-NMe2), 8.76 (1H, s, NHPh), 12.13 (1H, s, N(1)H). 13C
NMR (100 MHz, DMSO-d6): δ 34.1 (NMe), 40.1 (NMe), 115.4 (C-2′ and C-6′), 118.3 (C-4′), 128.4 (C-3′
and C-5′), 142.5 (C-1′), 157.0 (N=CH-NMe2), 158.1 and 158.3 (C-3 and C-5). Anal. Calcd for C11H14N6: C,
57.38; H, 6.13; N, 36.50. Found: C, 57.40; H, 6.22; N, 36.33.
N1,N1-Dimethyl-N2-[3(5)-methylpyrazol-5(3)-yl]formamidine (10a)
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Reaction time: 1 h. Yield 70%; mp 127-128 C (toluene), lit.:13 120-122 C. H NMR (400 MHz,
DMSO-d6): δ 2.08 (3H, br. s, Me), 2.86 (3H, br. s, NMe), 2.96 (3H, br. s, NMe), 5.56 (1H, br. s, H-4), 7.89
(1H, s, N=CH-NMe2), 11.62 (1H, br. s, N(1)H). 13C NMR (100 MHz, DMSO-d6): δ 10.9* and 14.0 (br. s,
Me), 33.8 (NMe), 39.5 (NMe), 88.8 and 94.2* (br. s, C-4), 138.3* (C-5), 146.7 (C-3), 152.6 (C-5), 154.2*
and 154.8 (br. s, N=CH-NMe2), 159.3* (C-3); *- signals of minor tautomeric form (KT = 1.15). Anal. Calcd
for C7H12N4: C, 55.24; H, 7.95; N, 36.81. Found: C, 55.27; H, 8.12; N, 36.60.
N1,N1-Dimethyl-N2-[3(5)-phenylpyrazol-5(3)-yl]formamidine (10b)
Reaction time: 1 h. Yield 96%; mp 177-179 C (toluene). 1H NMR (400 MHz, DMSO-d6): δ 2.92 (3H, s,
NMe), 3.02 (3H, s, NMe), 6.24 and 6.29* (1H, br. s, H-4), 7.25 (1H, br. t, J = 7.4 Hz, H-4′), 7.37 (2H, br. t,
J = 7.5 Hz, H-3′ and H-5′), 7.72 (2H, br. d, J = 7.6 Hz, H-2′ and H-6′), 8.04 (1H, s, N=CH-NMe2), 12.20 and
12.43* (1H, br. s, N(1)H); *- signals of minor tautomeric form (KT = 3.6). 13C NMR (100 MHz, DMSO-d6):
δ 33.8 (NMe), 39.6 (NMe), 86.1 (C-4), 134.5 (C-3′ and C-5′), 126.8 (C-4′), 128.3 (C-2′ and C-6′), 134.6
(C-1′), 149.6 (C-3), 153.4 (C-5), 155.5 (N=CH-NMe2). Anal. Calcd for C12H14N4: C, 67.27; H, 6.59; N,