3-(4-Nitrophenyl)-1,3,5-tris(5-tetrazolyl)pentane (4). Yield 8.12 g (82%); mp 210.5-211.5°C
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(decomp., ethanol). H NMR spectrum, δ, ppm: 2.50-2.80 (8H, m, CH2CN4H and CH2CH2CN4H); 7.22-7.41
(4H, m, 4-NO2C6H4); 15.98 (3H, br. s, CN4H). 13C NMR spectrum, δ, ppm: 161.2 and 155.5 (C(5) in tetrazoles);
141.8, 128.9, 127.5, 126.8 (4-NO2C6H4); 67.2, 45.0 (Cquat); 34.3 (CH2CH2CN4H); 18.4 (CH2CN4H). IR spectrum,
ν, cm-1: 2900-3200 (NH), 1640, 1555, 1530, 1250, 1080, 790 (tetrazole). Found, %: C 41.93; H 4.10; N 45.57.
C14H15N13O2. Calculated, %: C 42.32; H 3.80; N 45.82.
9,9-Bis[2-(5-tetrazolyl)ethyl]fluorene (5). Yield 7.70 g (86%); mp 280°C (decomp., ethanol). 1H NMR
spectrum, δ, ppm (J, Hz); 2.05 (4H, t, J = 9.4, CH2CN4H); 2.52 (4H, t, J = 9.4, CH2CH2CN4H); 7.30-8.00 (8H,
arom.); 15.60 (2H, br. s, CN4H). 13C NMR spectrum, δ, ppm: 155.6 (C(5) in tetrazole); 147.4, 140.8, 127.9,
123.3, 120.4, 54.1 (fluorene); 36.5 (CH2CH2CN4H); 18.2 (CH2CN4H). IR spectrum, ν, cm-1: 2900-3100 (NH),
1640, 1550, 1465, 1250, 1100, 770 (tetrazole). Found, %: C 63.31; H 5.38; N 30.96. C19H18N8. Calculated, %:
C 63.67; H 5.06; N 31.27.
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1,2-Bis[2-(5-tetrazolyl)ethoxy]propane (6). Yield 2.95 g (44%); mp 97-100°C (ethanol). H NMR
spectrum, δ, ppm (J, Hz): 1.08 (3H, d, J = 6.5, CHCH3); 3.05 (4H, t, J = 7.5, CH2CN4H); 3.28 (2H, d, J = 6.5,
CH2CHCH3); 3.50 (1H, m, J = 6.5, CH2CHCH3); 3.70 (4H, t, J = 7.5, CH2CH2CN4H); 15.80 (2H, br. s, CN4H).
13C NMR spectrum, δ, ppm: 154.1 (C(5) in tetrazole); 73.8 and 74.0 (CH2–CH); 67.6 and 65.5 (CH2CH2CN4H);
24.5 and 24.1 (CH2CN4H); 16.9 (CH3). IR spectrum, ν, cm-1: 3000-3200 (NH), 1605, 1570, 1550, 1450, 1340,
1250, 1120, 1050 (tetrazole). Found, %: C 39.98; H 6.27; N 41.56. C9H16N8O2. Calculated, %: C 40.29; H 6.01;
N 41.77.
Bis[2-(5-tetrazolyl)ethyl]amine Hydrochloride (7). Yield 4.17 g (68%); mp 152-154°C (decomp.,
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ethanol). H NMR spectrum, δ, ppm: 3.05 (4H, br. s, CH2CN4H); 3.70 (4H, br. s, CH2CH2CN4H); 9.00 (1H, s,
NH); 16.00 (2H, br. s, CN4H). 13C NMR spectrum, δ, ppm: 154.3 (C(5) in tetrazole); 66.7 (CH2CH2CN4H); 23.5
(CH2CN4H). IR spectrum, cm-1: 3000-3200, 2200-2800 (NH), 1560, 1450, 1380, 1255, 1100, 950 (tetrazole).
Found, %: C 29.20; H 5.16; N 51.08. C6H11N9·HCl. Calculated, %: C 29.33; H 4.92; 51.31.
Bis[2-(5-tetrazolyl)ethyl]amide of 4-Nitrobenzoic Acid (8). Yield 5.07 g (85%); mp 73-74°C
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(decomp., methanol). H NMR spectrum, δ, ppm (J, Hz): 3.00 and 3.12 (4H, t, J = 7.5, CH2CN4H); 3.60 and
3.82 (4H, t, J = 7.5, CH2CH2CN4H); 7.40 (2H, d, J = 4.0, 4-NO2C6H4); 8.22 (2H, d, J = 4.0, 4-NO2C6H4); 16.00
(2H, br. s, CN4H). 13C NMR spectrum, δ, ppm: 169.1 (CON); 154.0 (C(5) in tetrazole); 147.8, 142.4, 127.7,
123.9 (4-NO2C6H4); 46.5 and 42.3 (CH2CH2CN4H); 22.3 and 21.2 (CH2CN4H). IR spectrum, ν, cm-1: 2900-3200
(NH), 1760 (COO), 1645, 1550, 1535, 1250, 1100, 780. Found, %: C 43.14; H 4.15; N 38.73. C13H14N10O3.
Calculated, %: C 43.58; H 3.94; N 39.09.
Bis[2-(5-tetrazolyl)ethyl]malonic Acid (9). A solution of ditetrazole 11 (3.52 g, 10 mmol) and NaOH
(4.0 g, 100 mmol) in water (50 ml) was boiled for 10 h, cooled, and acidified to pH 1 with dilute hydrochloric
acid. The precipitated solid was filtered off, washed with distilled water, dried, and crystallized from ethyl
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acetate. Compound 9 was obtained (2.52 g, 85%); mp 172-173°C (decomp., ethyl acetate). H NMR spectrum,
δ, ppm (J, Hz): 2.25 (4H, t, J = 7.0, CH2CN4H); 2.85 (4H, t, J = 7.0, CH2CH2CN4H); 8.00-18.00 (4H, br. s,
CN4H and COOH). 13C NMR spectrum, δ, ppm: 172.1 (COOH), 155.5 (C(5) in tetrazole); 56.0 (Cquat); 29.8
(CH2CH2CN4H); 18.6 (CH2CN4H). IR spectrum, ν, cm-1: 2900-3200 (NH and OH), 1760 (COO), 1645, 1550,
1535, 1250, 1100, 780. Found, %: C 36.05; H 4.22; N 37.54. C9H12N8O4. Calculated, %: C 36.49; H 4.08;
N 37.82.
The work was carried out with the financial support of the Ministry of Education of the Russian
Federation for fundamental investigations in the area of technical sciences (TOO 2-09.3-3222).
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