Multi-step reaction with 12 steps
1.1: sulfuric acid / 24 h / 50 - 80 °C / Sealed tube
2.1: DBN / methanol / 12 h / 20 °C
3.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
3.2: 8 h / Inert atmosphere
4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
6.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
6.2: 12 h / Inert atmosphere
7.1: dimethylaluminum chloride / dichloromethane; hexane / 3 h / 20 °C / Inert atmosphere
8.1: pyridine / 24 h / 20 °C / Inert atmosphere
9.1: sodium azide / N,N-dimethyl-formamide / 150 °C / Microwave irradiation
10.1: copper(ll) sulfate pentahydrate / methanol / 8 h / 50 °C / Sealed tube
11.1: copper(l) iodide; sodium hydroxide / methanol; water / 50 °C
12.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
12.2: Inert atmosphere
With
pyridine; 1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; copper(ll) sulfate pentahydrate; sulfuric acid; DBN; dimethylaluminum chloride; toluene-4-sulfonic acid; sodium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2013.03.069