Scheme 5a.
aReagents and conditions: (a) H2CO, H2O, HCl, AcOH, 120 °C-r.t.; (b) BnBr, K2CO3, acetone, 56 °C; (c) i. KOH, H2O, r.t., ii. KMnO4, H2O, 0 °C-r.t., iii. EtOH, reflux; (d) AcCl, reflux; (e) 3-bromopropylamine HBr, Et 3N, Na2SO4, CHCl3, r.t.; (f) CHCl3, 0 °C - r.t.; (g) SOCl2, r.t.,(h) AlCl3 (2 eq.), nitrobenzene, 90 °C; (i), imidazole or morpholine, NaI, DMF, 70 °C.