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Reagents and conditions: (a)251 aq. HCl, reflux, 24 h; (b) (1) Na2S2O4, NaOH, H2O, 60 °C, 1 h, (2) CnH2n+1Br, Aliquat 336, toluene, 90 °C, 24 h; (c)252 (1) 2-octylthiophene and n-BuLi (premixed in Et2O at −78 °C for 1.5 h), −78 °C, then rt, overnight, (2) SnCl2·H2O, rt, 3 h; (d)253 MsOH, 150 °C, 16 h; (e) (1) NaH, DMF, rt, 2 h, (2) EtI, rt, 24 h; (f) N2H4·H2O, EtOH, 130 °C, 72 h; (g) toluene, 120 °C, 48 h.
