NOSACHEV et al.
580
(15) [M]+, 259 (10) [M – 1]+, 133 (30), 127 (100).
Found, %: C 73.63; H 4.38; N 21.31. C16H12N4. Calcu-
lated, %: C 73.85; H 4.62; N 21.54. M 260.32.
1,3-Diphenylaziridine-2,2-dicarbonitrile (Xa).
Yield 0.181 g (7%), Rf 0.54, mp 42–43°C. IR spec-
trum: ν 2250–2245 cm–1, m (C≡N). 1H NMR spectrum,
δ, ppm: 4.51 s (1H, CH), 7.74 m (10H, C6H5). Found,
%: C 78.19; H 4.32; N 16.98. C16H11N3. Calculated, %:
C 78.37; H 4.48; N 17.15.
Hydrolysis of 4,5-dihydro-1,2,3-triazole-4,4-di-
carbonitriles IV and V and 1H-1,2,3-triazolecarbo-
nitriles VI and VIIa (general procedure). A solution
of 6 mmol of compound IV–VII in 50 ml of concen-
trated hydrochloric acid was heated for 10 h under
reflux. The mixture was evaporated, and the residue
was subjected to column chromatography (see above)
using diethyl ether as eluent.
1-(4-Methylphenyl)-3-phenylaziridine-2,2-dicar-
bonitrile (Xb). Yield 0.162 g (6%), Rf 0.42, mp 85–
87°C. IR spectrum: ν 2250–2245 cm–1, m (C≡N).
1H NMR spectrum, δ, ppm: 2.10 s (3H, CH3), 4.52 s
(1H, CH), 6.95–7.25 m (4H, C6H4), 7.72 m (5H,
C6H5). Found, %: C 78.59; H 4.84; N 16.04. C17H13N3.
Calculated, %: C 78.77; H 5.02; N 16.21.
1,5-Diphenyl-1H-1,2,3-triazole-4-carboxylic acid
(VIIIa). Yield 0.782 g (52%), mp 131–132°C. IR spec-
1
trum, ν, cm–1: 3560 br (OH), 1740 s (C=O). H NMR
REFERENCES
spectrum, δ, ppm: 7.70 m (10H, C6H5), 13.55 s (OH).
Found, %: C 67.74; H 4.01; N 15.67. C15H11N3O2. Cal-
culated, %: C 67.92; H 4.15; N 15.85.
1. Grimmett, M.R., Comprehensive Organic Chemistry,
Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon,
1979, vol. 4. Translated under the title Obshchaya
organicheskaya khimiya, Moscow: Khimiya, 1985,
vol. 8, p. 429.
1,4-Diphenyl-1H-1,2,3-triazole-5-carboxylic acid
(IXa). Yield 0.827 g (55%), mp 111–112°C. IR spec-
1
trum, ν, cm–1: 3560 br (OH), 1740 s (C=O). H NMR
2. Varma, R.S. and Kabalka, G.W., Heterocycles, 1986,
spectrum, δ, ppm: 7.72 m (10H, C6H5), 13.23 s (OH).
Found, %: C 67.70; H 4.96; N 15.68. C15H11N3O2. Cal-
culated, %: C 67.92; H 4.15; N 15.85.
vol. 24, p. 2645.
3. Baran’ski, A. and Kelarev, V.I., Khim. Geterotsikl.
Soedin., 1990, p. 435.
1-(4-Methylphenyl)-5-phenyl-1H-1,2,3-triazole-
4-carboxylic acid (VIIIb). Yield 0.928 g (58%), mp
152–153°C. IR spectrum, ν, cm–1: 3560 br (OH), 1740
s (C=O). 1H NMR spectrum, δ, ppm: 2.10 s (3H, CH3),
6.95–7.25 m (4H, C6H4), 7.67 m (5H, C6H5), 13.56 s
(OH). Found, %: C 67.65; H 4.51; N 14.89.
C16H13N3O2. Calculated, %: C 68.82; H 4.66; N 15.05.
4. Joule, J.A. and Mills, K., Heterocyclic Chemistry,
Malden, MA: Blackwell Science, 2000, 4th ed. Trans-
lated under the title Khimiya geterotsiklicheskikh soedi-
nenii, Moscow: Mir, 2004, p. 728.
5. Nosachev, S.B., Tyrkova, E.A., and Tyrkov, A.G., Russ.
J. Org. Chem., 2009, vol. 45, p. 624.
6. Nosachev, S.B., Poddubnyi, O.Yu., Velikorodov, A.V.,
and Tyrkov, A.G., Russ. J. Org. Chem., 2010, vol. 46,
p. 674.
1-(4-Methylphenyl)-4-phenyl-1H-1,2,3-triazole-
5-carboxylic acid (IXb). Yield 0.842 g (53%),
mp 120°C. IR spectrum, ν, cm–1: 3560 br (OH), 1740 s
7. Kadaba, P.K., Tetrahedron, 1969, vol. 25, p. 3053.
8. Ershov, B.A., Spektroskopiya YaMR v organicheskoi
khimii (NMR Spectroscopy in Organic Chemistry), St.
Petersburg: Sankt-Peterb. Gos. Univ., 1995, p. 263.
9. Atkinson, R.S., Comprehensive Organic Chemistry,
Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon,
1979, vol. 2. Translated under the title Obshchaya
organicheskaya khimiya, Moscow: Khimiya, 1982,
vol. 3, p. 315.
10. Organikum. Organisch-chemisches Grundpraktikum,
Berlin: Wissenschaften, 1976, 15th edn. Translated
under the title Organikum. Praktikum po organicheskoi
khimii, Moscow: Mir, 1979, vol. 2, p. 150.
1
(C=O). H NMR spectrum, δ, ppm: 2.11 s (3H, CH3),
6.95–7.25 m (4H, C6H4), 7.67 m (5H, C6H5), 13.25 s
(OH). Found, %: C 67.62; H 4.48; N 14.85.
C16H13N3O2. Calculated, %: C 68.82; H 4.66; N 15.05.
Aziridine-2,2-dicarbonitriles Xa and Xb (general
procedure). A solution of 10 mmol of aryl azide IIIa or
IIIb in 50 ml of chloroform was added at 25°C to
a solution of 10 mmol of compound I or II in 100 ml
of chloroform. The mixture was heated for 5 h under
reflux and evaporated under reduced pressure, and the
residue was subjected to chromatography as described
above using carbon tetrachloride–benzene as eluent
(benzene was used as eluent for repeated chromatog-
raphy).
11. Solov’ev, N.A., Cand. Sci. (Chem.) Dissertation,
Leningrad, 1990.
12. Ugi, J., Perlinger, H., and Behringer, L., Chem. Ber.,
1958, vol. 91, p. 2330.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 4 2011