Multi-step reaction with 7 steps
1: 89 percent / NaHCO3 / acetone; H2O / 21 h / Ambient temperature
2: 1.) oxalyl chloride, DMSO, 2.) N-ethyldiisopropylamine / 1.) CH2Cl2, -60 to -50 deg C, 30 min, 2.) CH2Cl2, -50 deg C, 1 h
3: piperazine, AcOH / H2O / 1 h / Heating
4: 33 percent / Cu2O / toluene / 3 h / 40 °C
5: 100 percent / H2O / tetrahydrofuran / 4 h / Heating
6: 1,5-hexadiene, SOBr2 / 1,2-dichloro-ethane / a) 10 deg C, 1 h, b) RT, 1.5 h
7: 17 h / 80 °C / 75.01 Torr
With
piperazine; copper(I) oxide; sulfurous dibromide; oxalyl dichloride; 1,5-Hexadien; water; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; water; 1,2-dichloro-ethane; acetone; toluene;
DOI:10.1021/jm00075a029