*3.3. Synthesis of Propargyl Alcohols* **3a**,**c**,**d**,**f**

Acylethynylpyrrole **1a**,**c**,**d**,**f** (1 mmol) was dissolved in dry MeCN (4 mL), and then *t*-BuONa (192 mg, 2 mmol) was added to reaction mixture under nitrogen and reaction mixture was stirred at room temperature for 1 h. Then reaction mixture was diluted with water (30 mL) and extracted by diethyl ether (3 × 10 mL). Extracts were washed with water (3 × 5 mL) and dried over Na2SO4. The residue after removing solvents was fractionated by column chromatography (SiO2, *n*-hexane:diethyl ether, 10:1) to afford propargyl alcohol **3a**,**c**,**d**,**f**.

*5-(1-Benzyl-4,5,6,7-tetrahydro-1H-indol-2-yl)-3-hydroxy-3-(thiophen-2-yl)pent-4-ynenitrile* (**3a**). Spectral characteristics are the same as previously published [36].

*3-Hydroxy-3-phenyl-5-(1-vinyl-4,5,6,7-tetrahydro-1H-indol-2-yl)pent-4-ynenitrile* (**3c**). Yield: 224 mg (71%), yellow oil; 1H NMR (400.13 MHz, CDCl3): δ 7.72–7.71 (m, 2H, H*o*, Ph), 7.44–7.37 (m, 3H, H*m,p*, Ph), 6.98 (dd, *J* = 15.9, 9.3 Hz, 1H, Hx), 6.40 (s, 1H, H-3, pyrrole), 5.34 (d, *J* = 15.9 Hz, 1H, Ha), 4.88 (d, *J* = 9.3 Hz, 1H, Hb), 3.03 (d, *J* = 4.8 Hz, 2H, CH2CN), 2.85 (s, 1H, OH), 2.67–2.65 (m, 2H, CH2-7), 2.49–2.47 (m, 2H, CH2-4), 1.83–1.81 (m, 2H, CH2-5), 1.74–1.73 (m, 2H, CH2-6); 13C NMR (CDCl3, 100.6 MHz): δ 141.7, 131.5, 130.4, 129.0, 128.8 (2C), 125.4 (2C), 119.9, 117.3, 116.4, 111.3, 103.2, 92.9, 81.4, 71.0, 35.7, 24.1, 23.3, 23.1, 23.0. IR (film) 3422, 3062, 3030, 2931, 2851, 2215, 1643, 1492, 1447, 1383, 1295, 1241, 1143, 1102, 1053, 968, 910, 805, 765, 733, 700, 646 cm−1; Anal. Calcd for C21H20N2O: C, 79.72; H, 6.37; N, 8.85; O, 5.06%. Found: C, 79.44; H, 6.20; N, 8.59%.

*5-(4,5-Dimethyl-1-vinyl-1H-pyrrol-2-yl)-3-hydroxy-3-phenylpent-4-ynenitrile*(**3d**). Yield: 197 mg (68%), yellow crystals, mp 101–102 ◦C; 1H NMR (400.13 MHz, CDCl3): δ 7.72–7.70 (m, 2H, H*o*, Ph), 7.42–7.40 (m, 2H, H*m,p*, Ph), 6.91 (dd, *J* = 15.9, 9.1 Hz, 1H, Hx), 6.41 (s, 1H, H-3, pyrrole), 5.45 (d, *J* = 15.9 Hz, 1H, Ha), 4.99 (d, *J* = 9.1 Hz, 1H, Hb), 3.02 (d, *J* = 5.1 Hz, 2H, CH2CN), 2.86 (s, 1H, OH), 2.22 (s, 3H, Me), 2.00 (s, 3H, Me); 13C NMR (100.6 MHz, CDCl3): δ 141.7, 130.6, 128.9, 128.7 (2C), 128.6, 125.4 (2C), 119.5, 117.0, 116.4, 110.6, 105.6, 92.6, 81.4, 70.9, 35.6, 11.3, 11.1; IR (KBr) 3422, 3062, 3030, 2921, 2215, 1643, 1493, 1449, 1392, 1357, 1304, 1172, 1100, 1049, 967, 910, 809, 765, 733, 700, 634 cm<sup>−</sup>1; Anal. Calcd for C19H18N2O: C, 78.59; H, 6.25; N, 9.65; O, 5.51%. Found: C, 78.22; H, 6.02; N, 9.42%.

*3-Hydroxy-3-phenyl-5-(5-(4-methylphenyl)-1-vinyl-1H-pyrrol-2-yl)pent-4-ynenitrile* (**3f**). Yield: 281 mg (80%), yellow oil; 1H NMR (CDCl3, 400 MHz): δ 7.74–7.72 (m, 2H, H*o*, Ph), 7.45–7.39 (m, 2H, H*m,p*, Ph), 7.31 (d, *J* = 7.9 Hz, 2H, H*o*, C6H4), 7.21 (d, *J* = 7.9 Hz, 2H, H*m*, C6H4), 6.83 (dd, *J* = 15.8, 8.9 Hz, 1H, Hx), 6.67 (d, *J* = 3.8 Hz, 1H, H-4, pyrrole), 6.22 (d, *J* = 3.8 Hz, 1H, H-3, pyrrole), 5.52 (d, *J* = 15.8 Hz, 1H, Ha), 5.05 (d, *J* = 8.9 Hz, 1H, Hb), 3.06 (d, *J* = 5.0 Hz, 2H, CH2CN), 2.85 (s, 1H, OH), 2.39 (s, 3H, Me); 13C NMR (CDCl3, 100.6 MHz): δ 141.6, 137.8, 136.8, 131.2, 129.4, 129.3 (2C), 129.1 (3C), 128.8 (2C), 125.4 (2C), 118.9, 116.3, 113.7, 110.1, 108.0, 93.1, 81.4, 71.0, 35.6, 21.4; IR (KBr) 3416, 3061, 3028, 2922, 2218, 1643, 1515, 1472, 1449, 1418, 1389, 1324, 1301, 1224, 1112, 1042, 964, 909, 823, 773, 733,701, 622, 503 cm<sup>−</sup>1, Anal. Calcd for C24H20N2O: C, 81.79; H, 5.72; N, 7.95; O, 4.54%. Found: C, 81.35; H, 5.60; N, 7.68%.
