1: With potassium hydroxide in ethanol Alkylation; 0.75 h; Heating; 2: With lithium diisopropyl amide in tetrahydrofuran T=-78 - 20°C; Cyclization; 3.5 h;

1: With potassium hydroxide in ethanol Alkylation; 0.75 h; Heating; 2: With lithium diisopropyl amide in tetrahydrofuran T=-78 - 20°C; Cyclization; 3.5 h;

in toluene 24 h; Heating;

1: 72 percent / KOH / ethanol / 2 h / Ambient temperature 2: 90 percent / toluene / 24 h / Heating View Scheme

ammonium acetate; sodium cyanoborohydride 1) CH3OH, reflux, 3 h; 2) 280 deg C, 5 mm Hg, 20 min.; Yield given. Multistep reaction;

1: 1) BuLi / 1) THF, -78 deg C, 20 min; 2) THF, -78 deg C, 30 min. 2: 1) BuLi; 3) 0.5 M aq. HCl / 1) THF, -78 deg C; 2) THF, -78 deg C, 30 min; 3) reflux, 1 h. 3: 1) NaBH3CN, NH4OAc / 1) CH3OH, reflux, 3 h; 2) 280 deg C, 5 mm Hg, 20 min. View Scheme

1: 1) BuLi; 3) 0.5 M aq. HCl / 1) THF, -78 deg C; 2) THF, -78 deg C, 30 min; 3) reflux, 1 h. 2: 1) NaBH3CN, NH4OAc / 1) CH3OH, reflux, 3 h; 2) 280 deg C, 5 mm Hg, 20 min. View Scheme