5-Phenyl-2-tetrazolylacetic Acid N-Methylamide (4). Amide 4 (0.36 g, 37%) of mp 163-164°C was
obtained by crystallization from 20% aqueous ethanol (A), Rf 0.35 (CHCl3–MeOH, 95 : 5). IR spectrum, , cm-1:
ν
1404,1278, 1163, 1101 (tetrazole), 1449, 731 (C6H5), 1660 (C=O), 3303, 1578, 1528 (N–H), 2964, 2888 (CH2),
1388, 1073, 1025 (C–N). Found, %: C 55.65; H 5.57; N 32.26. C10H11N5O. Calculated, %: C 55.29; H 5.10;
N 32.24.
5-Phenyl-2-tetrazolylacetic Acid N,N-Dimethylamide (5). Amide 5 (0.65 g, 65%) of mp 133-134°C
was obtained by crystallization from 10% aqueous ethanol (B), Rf 0.36 (CHCl3–MeOH, 95 : 5). IR spectrum,
, cm-1: 1401, 1283, 1180, 1130 (tetrazole), 1451, 735 (C6H5), 1662 (C=O), 2969, 2933 (CH2), 1378, 1071, 1029
ν
(C–N). Found, %: C 56.95; H 5.97; N 30.06. C11H13N5O. Calculated, %: C 57.13; H 5.67; N 30.28.
5-Phenyl-2-tetrazolylacetic Acid N-Ethylamide (6). Amide 6 (0.86 g, 86%) of mp 151-152°C was
obtained by crystallization from 25% aqueous ethanol (A), Rf 0.45 (CHCl3–MeOH, 95 : 5). IR spectrum, , cm-1:
ν
1406, 1277, 1173, 1102 (tetrazole), 1447, 729 (C6H5), 1660 (C=O), 3287, 1560, 1527 (N–H), 2954, 2882 (CH2),
1381, 1070, 1022 (C–N). Found, %: C 57.69; H 6.01; N 30.67. C11H13N5O. Calculated, %: C 57.13; H 5.67;
N 30.28.
5-Phenyl-2-tetrazolylacetic Acid N-Cyclohexylamide (7). Amide 7 (0.71 g, 58%) of mp 173-174°C
was obtained by crystallization from 50% aqueous ethanol (B), Rf 0.62 (CHCl3–MeOH, 95 : 5). IR spectrum,
, cm-1: 1421, 1279, 1171, 1091 (tetrazole), 1447, 728 (C6H5), 1654 (C=O), 3291, 1556, 1528 (N–H), 2938,
ν
2851 (CH2), 1371, 1072, 1024 (C–N). Found, %: C 63.64; H 6.72; N 24.97. C15H19N5O. Calculated, %: C 63.14;
H 6.71; N 24.54.
5-Phenyl-2-tetrazolylacetic Acid N-1-Adamantylamide (8). Amide 8 (0.91 g, 54%) of mp 263-264°C
was obtained by crystallization from 20% aqueous ethanol (B), Rf 0.15 (CHCl3–MeOH, 9 : 1). IR spectrum,
, cm-1: 1418, 1279, 1177, 1110 (tetrazole), 1452, 730 (C6H5), 1632 (C=O), 1562, 1529 (N–H), 3006, 2935,
ν
2912, 2853 (CH2 and CH), 1073, 1026 (C–N). Found, %: C 66.98; H 6.83; N 20.23. C19H23N50. Calculated, %:
C 67.63; H 6.87; N 20.76.
N,N'-Bis(5-phenyl-2-tetrazolylmethylcarbonyl)-1,2-diaminoethane (9). Amide 9 (0.83 g, 44%) of
mp 255-256°C was obtained by crystallization from 40% aqueous ethanol (A), Rf 0.55 (CHCl3–MeOH, 9 : 1). IR
spectrum, , cm-1: 1415, 1284, 1194, 1104 (tetrazole), 1449, 728 (C6H5), 1664 (C=O), 3296, 1576, 1528 (N–H),
ν
2953, 2875 (CH2), 1364, 1072, 1027 (C–N). Found, %: C 55.77; H 4.44; N 32.61. C20H20N10O2. Calculated, %:
C 55.55; H 4.66; N 32.39.
The work was carried out with the financial support of the International Scientific Fund (grant r99-468)
and the Fund for the Administration of St. Petersburg (grants M2000-2.5D-572 and M2000-2.5P-573).
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