Scheme 1. Representative Synthetic Scheme for the Preparation of Bicyclic Aromatic Compounds 13a–l.
Shown for the quinoline-containing compound 13a. Reagents and conditions: (a) CH3NHOCH3·HCl, BOP, Et3N, CH2Cl2, rt, 2 h (88%); (b) DIBAL-H in hexanes, THF, – 78 °C, 2 h (assumed quant.); (c) NaBH(OAc)3, AcOH, DCE, rt, overnight (47%); (d) TFA, CH2Cl2, H2O, rt, 2 h, (86%). The variable group for compounds 6b–l, 7b–l, 8b–l, 12b–l, and 13b–l is indicated in blue.