Scheme 114. Azatriangulene Derivatives Bearing Peripheral sp3-Hybridized Carbon Atoms.
Reagents and conditions: (a)227 Cu, CuI, K2CO3, n-Bu2O, 150 °C, 48 h; (b) MeMgBr, toluene, 110 °C, 15 h; (c) 85% H3PO4, rt, 4 h; (d) tris(4-bromophenyl)ammoniumyl hexachloroantimonate (BAHA), DCM, N2, rt, 1 h; (e)228 benzene, 80 °C, 24 h; (f) AcOH, H2O, HCl, 100 °C, 12 h; (g) benzene/n-BuOH/pyridine, Dean–Stark apparatus, reflux, 5 h.