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1-(N-Benzyl-N-nitrosoamino)-5-phenyltetrazole (23). H NMR spectrum (DMSO-d6), δ, ppm: 5.86
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(2H, br. s, CH2); 7.25-7.33 (5H, m, C6H5); 7.46-7.60 (5H, m, CH2C6H5). H NMR spectrum (CDCl3), δ, ppm:
5.50 (2H, br. s, CH2); 6.95 (2H, m, o-HCH Ph); 7.05-7.35 (6H, m, m-,p-HPh and m-,p-HCH Ph); 7.50 (2H, m, o-HPh).
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Found, %: C 60.11; H 4.39; N 29.87. C14H12N6O. Calculated, %: C 59.99; H 4.32; N 29.98.
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2-(N-Benzyl-N-nitrosoamino)-5-phenyltetrazole (24). H NMR spectrum (DMSO-d6), δ, ppm: 5.85
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(2H, br. s, CH2); 7.38 (5H, s, CH2C6H5); 7.61 (3H, m, m-,p-HPh); 8.06 (2H, m, o-HPh). H NMR spectrum
(CDCl3), δ, ppm: 5.58 (2H, s, CH2); 7.31 (5H, s, CH2C6H5); 7.48 (3H, m, m-, p-HPh); 8.10 (2H, m, o-HPh).
Found, %: C 59.89; H 4.39; N 30.09. C14H12N6O. Calculated, %: C 59.99; H 4.32; N 29.98.
1-(N-Benzyl-N-nitrosoamino)benzotriazole (25). 1H NMR spectrum (DMSO-d6), δ, ppm: 5.47 (2H, br.
s, CH2, E); 6.18 (2H, br. s, CH2, Z); 7.10-7.66 (8H, m, CH2C6H5, H-5,7, E + Z); 8.13 (1H, m, H-4, E + Z).
1H NMR spectrum (CDCl3), δ, ppm: 5.40 (2H, br. s, CH2, E); 5.96 (2H, br. s, CH2, Z); 6.66 (1H, m, H-7, E + Z);
7.35 (7H, m, CH2C6H5, H-5,6, E + Z); 8.04 (1H, m, H-4, E + Z). Found, %: C 61.57; H 4.44; N 27.79.
C13H11N5O. Calculated, %: C 61.65; H 4.38; N 27.65.
1-(N-Benzyl-N-nitrosoamino)-3-methylbenzimidazol-2-one (26). 1H NMR spectrum (DMSO-d6),
δ, ppm (J, Hz): 3.33 (3H, s, CH3, Z); 3.39 (3H, s, CH3, E); 5.19 (2H, br. s, CH2, E); 5.50 (1H, d, J = 14.6, CH2,
Z); 6.20 (1H, d, J = 14.6, CH2, Z); 6.24 (1H, d, J = 7.5, H-7, Z); 6.75 (1H, d, J = 7.5, H-7, E); 6.85 (1H, dt,
3J = 7.8, 4J = 1.3, H-6, Z); 7.00-7.26 (2H, m, H-4, 5, E + Z); 7.36 (3H, m, m-, p-HPh, E + Z); 7.52 (2H, m, o-HPh,
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E + Z). H NMR spectrum (CDCl3), δ, ppm (J, Hz): 3.39 (3H, s, CH3, Z); 3.45 (3H, s, CH3, E); 5.16 (2H, br. s,
CH2, E); 5.34 (1H, d, J = 14.7, CH2, Z); 5.98 (1H, d, J = 7.7, H-7, Z); 6.22 (1H, d, J = 14.7, CH2, Z); 6.41 (1H, d,
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J = 7.7, H-7, E); 6.77 (1H, dt, J = 7.7, J = 0.8, H-6, Z); 6.90-7.24 (2H, m, H-4, 5, E + Z); 7.21 (3H, m,
m-, p-HPh, E + Z); 7.33 (2H, m, o-HPh, E + Z). Found, %: C 63.95; H 4.87; N 19.73. C15H14N4O2. Calculated, %:
C 63.82; H 5.00; N 19.85.
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7-(N-Benzyl-N-nitrosoamino)-8-methyltheophylline (27). H NMR spectrum (DMSO-d6), δ, ppm
(J, Hz): 1.50 (3H, s, C-CH3, Z); 1.89 (3H, s, C-CH3, E); 3.19 (3H, s, N-CH3, Z); 3.23 (3H, s, CH3, E); 3.35 (3H,
s, N-CH3, Z); 3.40 (3H, s, CH3, E); 4.26 (1H, d, J = 14.4, CH2, E); 5.38 (1H, d, J = 14.4, CH2, Z); 6.13 (1H, d,
J = 14.4, CH2, E); 6.41 (1H, d, J = 14.4, CH2, Z); 7.36 (5H, m, C6H5, E + Z). 1H NMR spectrum (CDCl3), δ, ppm
(J, Hz): 1.49 (3H, s, C-CH3, Z); 1.82 (3H, s, C-CH3, E); 3.36 (3H, s, N-CH3, Z); 3.39 (3H, s, CH3, E); 3.52 (3H,
s, N-CH3, Z); 3.56 (3H, s, CH3, E); 4.43 (1H, d, J = 14.4, CH2, E); 5.33 (1H, d, J = 14.4, CH2, Z); 5.93 (1H, d,
J = 14.4, CH2, E); 6.47 (1H, d, J = 14.4, CH2, Z); 7.19 (2H, m, o-HPh, E); 7.31 (3H, m, m-, p-HPh, E); 7.46 (5H,
m, C6H5, Z). Found, %: C 54.73; H 4.79; N 25.48. C15H16N6O3. Calculated, %: C 54.87; H 4.91; N 25.60.
1-(N-Acetylamino)indazole (29). Acetyl chloride (0.6 g, 12 mmol) was added to a solution of
1-aminoindazole (1.33 g, 10 mmol) in ether (6 ml), the mixture was left for 15 min, the ether evaporated, and the
residue was neutralized with conc. ammonia solution. The solid was filtered off. Compound 29 (0.40 g, 23%)
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was obtained as colorless crystals of mp 132-133°C (octane). H NMR spectrum CDCl3), δ, ppm (J, Hz): 1.75
(3H, s, CH3, E); 2.21 (3H, s, CH3, Z); 7.45 (3H, m, H-4, 6, E + Z); 7.71 (1H, d, J = 8.2, H-7, E + Z); 7.99 (1H, s,
H-3, Z); 8.10 (1H, s, H-3, E); 8.40 (1H, br. s, NH, Z); 9.00 (1H, br. s, NH, E). IR spectrum, ν, cm-1: 3260 (NH),
1690 (CO). Found, %: C 61.81; H 5.32; N 23.84. C9H9N3O. Calculated, %: C 61.70; H 5.18; N 23.99.
1-(N-Acetyl-N-methylamino)indazole (30). Potassium hydroxide (0.067 g, 1.2 mmol) was added to a
solution of 1-(N-acetylamino)indazole (29) (0.175 g, 1 mmol) in acetone (10 ml), the mixture was stirred for
15 min, iodomethane (0.1 ml, 1.5 mmol) was added, and the mixture stirred for a further 3 h. The acetone was
distilled off (to 1/3 volume), chloroform (10 ml) was added to the remainder, the mixture was filtered, and the
chloroform solution was chromatographed on a column of Al2O3, eluent was chloroform, collecting the fraction
with Rf 0.65. After evaporating the chloroform, compound 30 (0.087 g, 46%) was obtained as a dark yellow oil.
1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 1.75 (3H, s, COCH3); 3.89 (3H, s, N-CH3); 7.26 (1H, m, H-5); 7.35
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(1H, m, H-4); 7.49 (1H, m, H-6); 7.76 (1H, d, J = 8.0, H-7); 8.03 (1H, d, J = 0.8, H-3). IR spectrum, ν, cm-1:
1700 (CO). Found, %: C 63.62; H 5.79; N 22.41. C10H11N3O. Calculated, %: C 63.48; H 5.86; N 22.21.
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