(Csp); 114.7 (CPy); 117.7 (CPy-H); 127.4, 128.3, 129.2, 129.4, 129.8, 129.9, 138.8, 140.(CPh); 152.5; 155.6; 160.9
(CPy). 13C {1H} spectrum (75 MHz, CDCl3), δ, ppm (J, Hz); 117.7 (d, J = 169, CPy-H). Mass spectrum, m/z, (Irel,
%): 458 (100) [M+1]+, 457 (20) [M]+, 414 (15), 400 (20), 358 (40), 344 (43), 330 (56), 136 (53), 103 (77), 77
(55). Found, %: C 88.74; H 7.95; N 2.52. C34H35N. Calculated, %: C 89.23; H 7.71; N 3.06.
4-(Dec-2-ynyl)- 2,6-diphenyl-3-(undeca-1,3-diynyl)pyridine (4b) was obtained from dodeca-5,7-diyne
(1b) [10] (0.81 g, 5 mmol) and benzonitrile (0.515 g, 5 mmol). The product (0.94 g, 74%) was isolated by PTLC
(eluent was hexane–CH2Cl2, 1:1). Oily liquid, Rf 0.89 (hexane–CH2Cl2, 1:1). Also a fraction (0.12 g, 9%) was
isolated, containing 3b, Rf 0.86 (hexane–CH2Cl2, 1:1). IR spectrum, ν, cm-1: 3080, 3030, 2960, 2850, 2240,
1580, 1570, 1470. 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 0.89 (3H, t, J = 7, CH3); 0.92 (3H, t, J = 7, CH3);
1.20-1.65 [20H, m, 2(CH2)5]; 2.31 (2H, t, J = 6, ≡CCH2); 2.39 (2H, t, J = 7, ≡CC≡CCH2); 3.81 (2H, s, CH2C≡);
7.40-7.55 (6H, m, H-CPh); 7.95 (2H, d, J = 6, H-CPh); 8.14 (2H, d, J = 6, H-CPh); 8.05 (1H, s, H-CPy). 13C NMR
spectrum (CDCl3), δ, ppm: 13.9; 14.2; 19.0, 19.8 (2 ≡CCH2); 22.8 (CH2C≡); 22.9; 24.9; 25.0; 28.3; 28.4; 29.0;
29.3; 29.5; 32.0; 32.1; 65.3, 70.6, 84.4, 85.2, 85.4, 88.7 (Csp); 114.7 (CPy); 117.6 (CPy-H); 127.4, 128.3, 129.2,
13
129.4, 129.8, 129.9, 138.8, 140.0 (CPh); 152,5, 155.6, 160.9 (CPy). C {1H} spectrum (CDCl3), δ, ppm (J, Hz):
117.3 (d, J = 169, CPy-H). Mass spectrum, m/z (Irel, %): 513 (31) [M]+, 456 (12), 442 (22), 428 (41), 414 (53), 358
(47), 344 (66), 330 (100), 318 (37), 280 (16), 264 (18), 252 (18), 239 (16), 105 (22), 91 (38). Found, %:
C 88.84; H 8.32; N 2.89. C38H43N. Calculated, %: C 88.84; H 8.44; N 2.73.
2,6-Bis(4-methoxyphenyl)-3-(nona-1,3-diynyl)-4-(oct-2-ynyl)pyridine (4c) was obtained from
compound 1a (0.67 g, 5 mmol) and 4-methoxybenzonitrile (0.67 g, 5 mmol). The product was isolated by
column chromatography (gradient elution: hexane–hexane:Et2O, 7:1). Yield was 1.29 g (90%). Mp 61-63°C
(from hexane), Rf 0.77 (hexane–Et2O, 3:1). A fraction (0.09 g) was also isolated, containing according to NMR
spectra, compound 4c and 3c in a 5:2 ratio. IR spectrum, ν, cm-1: 3070, 3000, 2955, 2870, 2230, 1730, 1600,
1400, 1370, 1340, 1290, 1230, 1100, 1020, 810. 1H NMR spectrum (CDCl3), δ, ppm (J, Hz): 0.95 (3H, t, J = 7,
CH3); 0.97 (3H, t, J = 7, CH3); 1.30-1.63 [12H, m, 2(CH2)3]; 2.31 (2H, t, J = 7, ≡CCH2); 2.39 (2H, t, J = 7,
≡CC≡CCH2); 3.86 (2H, s, CH2C≡); 3.89 (3H, s, CPh-OCH3); 3.91 (3H, s, CPh-OCH3); 7.00 (2H, d, J = 9, CPh-H);
7.03 (2H, d, J = 9, CPh-H); 7.96 (1H, s, H-CPy); 8.07 (2H, d, J = 9, CPh-H); 8.12 (2H, d, J = 9, CPh-H). 13C NMR
spectrum (CDCl3), δ, ppm: 14.3; 14.4; 19.3, 20.2 (2 ≡CCH2); 22.6; 22.7 (CH2C≡); 25.0; 28.8; 29.1; 31.6; 31.8;
55.7 (2CH3O); 65.6, 71.3, 75.9, 77.9, 85.1, 88.0 (Csp); 113.3 (CPy); 113.7, 114.5 (CPh); 116.4 (CPy-H); 131.3,
131.7, 131.9, 132.8 (CPh); 152.2 (CPy); 155.3, 160.3 (CPh); 160.7, 161.2 (CPy). Mass spectrum, m/z (Irel, %): 518
(88) [M+1]+, 517 (38) [M]+, 488 (10), 474 (24), 460 (38), 446 (64), 432 (18), 304 (52), 105 (100), 91 (14), 77
(44). Found, %: C 83.17; H 8.05; N 2.72. C36H39NO2. Calculated, %: C 83.52; H 7.59; N 2.71.
4-(Dec-2-ynyl)-2,6-bis(4-tolyl)-3-(undeca-1,3-diynyl)pyridine (4d) was obtained from compound 1b
(0.81 g, 5 mmol) and 4-methylbenzonitrile (0.587 g, 5 mmol). Pyridine 4d (0.79 g, 69%) and dodecadiyne (0.17
g, 21%) were isolated by PTLC (eluting system hexane–Et2O, 4:1). Oily liquid, Rf 0.74 (hexane–Et2O, 4:1).
1
IR spectrum, ν, cm-1: 3090, 3070, 3045, 2965, 2930, 2855, 2235, 2210, 1560, 1520, 1445, 1420. H NMR
spectrum (CD2Cl2), δ, ppm (J, Hz): 0.89 (3H, t, J = 7, CH3); 1.20-1.67 [10H, m, (CH2)5]; 2.34 (2H, t, J = 7,
≡CCH2); 2.39 (2H, t, J = 7, ≡CC≡CCH2); 2.42 (3H, s, CPh-CH3); 2.45 (3H, s, CPh-CH3); 3.82 (2H, s, CH2C≡);
7.31 (4H, m, CPh-H); 7.88 (2H, d, J = 9, CPh-H); 8.03 (2H, d, J = 9, CPh-H); 8.01 (1H, s, H-CPy). 13C NMR
spectrum (CD2Cl2), δ, ppm: 14.3; 14.4; 19.1, 19.9 (2 ≡CCH2); 21.2 (CH2C≡); 21.3; 22.9; 23.0; 24.8; 28.5; 29.0;
29.1, 29.2; 29.3, 29.5 (2CH3); 32.0; 32.1; 65.0, 70.8, 75.6, 83.2, 84.0, 85.1 (Csp); 110.5 (CPy); 116.3 (CPy-H);
127.3, 128.9, 129.6, 129.8, 137.3, 139.4, 140.1 (CPh); 152.4 (CAr); 155.6 (CAr); 156.9, 158.2 (CPy). Mass
spectrum, m/z (Irel, %): 541 (11) [M]+, 111 (15), 85 (33), 69 (100), 57 (77), 55 (40).
2,6-Bis(3,4-dimethoxyphenyl)-3-(nona-1,3-diynyl)-4-(oct-2-ynyl)pyridine (4e) was obtained from
compound 1a (0.67 g, 5 mmol) and 3,4-dimethoxybenzonitrile (0.815 g, 5 mmol). Compound 4e (0.704 g, 59%)
and 1,3-decadiyne (0.11 g, 17%) were isolated by column chromatography (gradient elution hexane–hexane:
Et2O, 3:1). Yellow crystalline substance, mp 61-63°C (chloroform). Rf 0.69 (hexane–Et2O, 3:1). IR spectrum,
ν, cm-1: 3025, 2980, 2955, 2890, 2875, 2855, 2250, 1610, 1515, 1470, 1425. 1H NMR spectrum (CDCl3), δ, ppm
621