2-[1H-Indol-3-yl(phenyl)methyl]cyclopentanone (4b) (R*,S*). White crystals; mp 182-184°C
(aqueous 2-propanol). 1H NMR spectrum, δ, ppm (J, Hz): 1.6-1.9 [6H, m, (CH2)3]; 3.02 (1H, m, CHCHPh); 4.72
(1H, d, J = 5.37, CHPh); 6.86 (1H, m, H-5Ind); 7.06 (1H, m, H-6Ind); 7.1-7.2 (6H, m, Ph and Ind); 7.29 (1H, d,
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J = 2.19, H-2Ind); 7.36 (1H, m, H-7Ind); 10.77 (1H, s, NH). H NMR spectrum (C5D5N), δ, ppm (J, Hz): 1.5-2.2
[6H, m, (CH2)3]; 3.12 (1H, m, CHCHPh); 5.28 (1H, d, J = 3.97, CHPh); 7.05 (1H, m, H-5Ind); 7.25 (3H, m, HPh);
7.25 (1H, m, H-6Ind); 7.43 (2H, m, o-HPh); 7.48 (1H, m, H-4Ind); 7.55 (1H, m, H-7Ind); 7.62 (1H, dd, J = 2.45,
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J = 0.6, H-2Ind); 11.97 (1H, s, NH). Characteristic signal for the (R*,R*)-isomer in the H NMR spectrum
(C5D5N), δ, ppm: 5.14 (1H, d, J = 3.97, CHPh). Mass spectrum, m/z (Irel, %): 289 (22) [M]+, 205 (100)
[IndCHPh]+. Found, %: C 83.2; H 6.73; N 4.41. C20H19NO. Calculated, %: C 83.01; H 6.62; N 4.84.
2-Hydroxy-3-[1H-indol-3-yl(phenyl)methyl]-2-cyclohexen-1-one (4c). White crystals; mp 121-123°C
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(aqueous 2-propanol). H NMR spectrum, δ, ppm (J, Hz): 1.92-2.50 (6H, m, cyclohexane); 5.9 (1H, s,
IndCHPh); 6.32 (1H, s, OH); 6.86 (1H, d, J = 7.2, H-2Ind); 7.05 (1H, m, H-5Ind); 7.2-7.3 (7H, m, Ind and Ph);
7.37 (1H, m, H-4Ind); 7.57 (1H, m, H-7Ind); 8.08 (1H, br. s, NH). Mass spectrum, m/z (Irel, %): 317 (20) [M]+, 206
(100) [IndCHPh]+. Found, %: C 80.2; H 6.43; N 4.21. C21H19NO2. Calculated, %: C 79.47; H 6.03; N 4.41.
2-[1H-Indol-3-yl(phenyl)methyl]-3-oxobutyric Acid Methyl Ester (4f). White crystals;
mp 147-149°C (aqueous 2-propanol). 1H NMR spectrum, δ, ppm (J, Hz): 2.07-2.16 (3H, m, COCH3); 3.51-3.55
(3H, m, OCH3); 4.64-4.73 (1H, m, IndCHPhCH); 5.01-5.03 (1H, m, IndCHPh); 7.01 (1H, m, H-5Ind); 7.11 (1H,
m, H-6Ind); 7.17 (1H, m, p-HPh); 7.27 (2H, m, m-HPh); 7.29 (1H, m, H-2Ind); 7.37 (1H, m, H-7Ind); 7.42 (2H, m,
o-HPh); 7.57 (1H, m, H-4Ind); 9.02 (1H, br. s, NH). Mass spectrum, m/z (Irel, %): 321 (24) [M]+, 206 (100)
[IndCHPh]+. Found, %: C 74.95; H 6.07; N 4.26. C20H19NO3. Calculated, %: C 74.75; H 5.96; N 4.36.
2-[1H-Indol-3-yl(phenyl)methyl]-3-oxobutyric Acid Isopropyl Ester (4h). White crystals;
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mp 111-119°C (aqueous 2-propanol). H NMR spectrum, δ, ppm (J, Hz): 0.94-1.11 [6H, m, (CH3)2]; 2.10-2.18
(3H, m, COCH3); 4.79 (1H, m, OCH); 4.58-4.68 (1H, m, IndCHPhCH); 4.99-5.01 (1H, m, IndCHPh); 7.00 (1H,
m, H-5Ind); 7.11 (1H, m, H-6Ind); 7.16 (1H, m, p-HPh); 7.27 (2H, m, m-HPh); 7.31 (1H, m, H-2Ind); 7.37 (1H, m,
H-7Ind); 7.43 (2H, m, o-HPh); 7.59 (1H, m, H-4Ind); 9.21 (1H, br. s, NH). Mass spectrum, (Irel, %): 349 (18) [M]+,
206 (100) [IndCHPh]+. Found, %: C 75.82; H 6.83; N 3.93. C22H23NO3. Calculated, %: C 75.62; H 6.63; N 4.01.
2-Cyano-3-(1H-indol-3-yl)-3-phenylpropionic Acid Methyl Ester (4m). White crystals;
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mp 146-147°C (aqueous AcOH). H NMR spectrum, δ, ppm (J, Hz): 3.56 (3H, s, CH3); 5.25 (1H, d, J = 7.2,
CNCHCOCH3); 5.57 (1H, d, J = 7.2, IndCHPh); 7.1-7.7 (9H, m, Ind and Ph); 8.11 (1H, m, H-2Ind); 12.36 (1H,
br. s, NH). Mass spectrum, m/z (Irel, %): 304 (14) [M]+, 206 (90) [IndCHPh]+. Found, %: C 75.01; H 5.2; N 9.15.
C19H16N2O2. Calculated, %: C 74.98; H 5.3; N 9.2.
2-Cyano-3-(1H-indol-3-yl)-3-phenylpropionic Acid Ethyl Ester (4n). White crystals; mp 91-93°C
(aqueous AcOH). 1H NMR spectrum, δ, ppm (J, Hz): 0.97-1.00 (3H, m, CH2CH3); 4.02-4.05 (2H, m, CH2CH3);
4.92-4.95 (1H, m, CNCHCOEt); 5.00-5.09 (1H, m, IndCHPh); 7.1-7.8 (10H, m, Ind and Ph); 10.97 (1H, br. s,
NH). Mass spectrum m/z, (Irel, %): 318 (8) [M]+, 206 (90) [IndCHPh]+. Found, %: C 75.57; H 5.58; N 8.70.
C20H18N2O2. Calculated, %: C 75.45; H 5.70; N 8.80.
(2S*)-2-[(R*)-1H-Indol-3-yl(phenyl)methyl]-3,4-dihydro-1-(2H)-naphthalenone (4o). White crystals;
mp 138-139°C (aqueous 2-propanol). Mass spectrum m/z (Irel, %): 351 (17) [M]+, 206 (100) [IndCHPh]+.
Found, %: C 85.63; H 6.04; 3.87. C25H21NO. Calculated, %: C 85.44; H 6.02; N 3.99.
2-[1H-Indol-3-yl(phenyl)methyl]cyclopentanone Hydrazone (5). Compound 4b (0.303 g, 0.1 mmol)
and anhydrous hydrazine hydrate (0.64 g, 20 mmol) were mixed in alcohol (5 ml). The mixture was maintained
at room temperature until disappearance of the starting material (check by TLC on Silufol UV 254, ethyl
acetate–CCl4, 1:4). The reaction mixture was poured into water and the white crystals were filtered off;
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mp 162-163°C (aqueous 2-propanol). H NMR spectrum, δ, ppm: 1.65-2.4 (6H, m, cyclopentyl); 3.35-3.6 (1H,
m, IndCHPhCH); 4.57-4.59 (1H, m, IndCHPh); 6.9-7.3 (9H, m, Ind and Ph); 7.2 (1H, m, H-2Ind); 9.1-9.18 (1H,
br. s, NH). Mass spectrum, m/z (Irel, %): 303 (25) [M]+, 206 (100) [IndCHPh]+. Found, %: C 80.03; H 7.04;
N 12.93. C20H21N3. Calculated, %: C 79.17; H 6.98; N 13.85.
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