Multi-step reaction with 6 steps
1: 1) H2SO4, NaNO2, 2) NaN3 / 1) H2O, 0 deg C, 30 min, 2) 3 h
2: pyridinium chlorochromate / CH2Cl2 / 4 h / Ambient temperature
3: 67 percent / Na, EtOH / 5 h / -15 °C
4: 91 percent / diethyl ether / 12 h / Ambient temperature
5: 83 percent / CH2Cl2 / Ambient temperature; 1 equiv of isocyanate (reaction with 2 equiv of isocyanate, toluene, r.t., 1 h, then 160 deg, 1h leads directly to pyrido<2,3,4-de>quinazolines); sequential treatment with isocyanate and ketene or aldehydes and isocyanates; reaction with CS2
6: toluene / 1) room temperature, 30 min, 2) 160 deg C, 24 h
With
sodium azide; ethanol; sulfuric acid; sodium; pyridinium chlorochromate; sodium nitrite;
In
diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo00051a007