Research Article
Regioselective 5-exo-Trig Heterocyclization of 2-Allyl-1-naphthols under the Influence of N-Iodosuccinimide or Molecular Iodine in Aqueous Micelle
Scheme 1
Iodocyclization of different 2-allylhydroxy naphthalene derivatives. Reagents and conditions: (i) R1R2C=CR3–CH2X (X = Br, Cl), Me2CO, K2CO3, NaI, reflux, 6–8 h; (ii) o-DCB, reflux, 8–10 h; (iii) Condition A: substrates 3(a–e) (0.5 mmol), NIS (0.5 mmol), MeCN (15 mL), 0°C-r.t, 3 h; Condition B: substrates 3(a–e) (0.5 mmol), I2 (1.4 equiv.), CTAB (0.30 mmol), H2O (10 mL), r.t, 8 h; (iv) KOH (1.0 mmol), EtOH (5 mL), reflux, 2 h.
