1: 2) dil. aq. hydrochloric acid / 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight 2: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 3: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 4: 82 percent / diethyl ether / 0.25 h / 0 °C 5: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 6: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 7: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 8: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 9: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 10: 95 percent / aq. sodium hydroxide / 0.08 h View Scheme

1: 2) dil. aq. hydrochloric acid / 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight 2: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 3: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 4: 82 percent / diethyl ether / 0.25 h / 0 °C 5: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 6: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 7: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 8: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 9: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 10: 95 percent / aq. sodium hydroxide / 0.08 h 11: 86 percent / diethyl ether / 3 h / 0 °C 12: CDCl3 / 3 h / 55 °C 13: methanol View Scheme

in tetrahydrofuran 3 h; Heating;

hydrogenchloride 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight; Yield given. Multistep reaction;

Multistep reaction;

ammonia in methanol T=40°C; 2 h; Yield given;

hydrogenchloride in tetrahydrofuran

1: 2) dil. aq. hydrochloric acid / 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight 2: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 3: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 4: 82 percent / diethyl ether / 0.25 h / 0 °C 5: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 6: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 7: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 8: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 9: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C View Scheme

1)ether,reflux 2)2M HCl, room temperature, 16h; Yield given. Multistep reaction;

1: 2) dil. aq. hydrochloric acid / 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight 2: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 3: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 4: 82 percent / diethyl ether / 0.25 h / 0 °C 5: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 6: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 7: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 8: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature View Scheme