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. 2021 Aug 23;64(17):12938–12963. doi: 10.1021/acs.jmedchem.1c01094

Scheme 1. Representative Synthetic Scheme for the Preparation of Bicyclic Aromatic Compounds 13al.

Scheme 1

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 6bl, 7bl, 8bl, 12bl, and 13bl is indicated in blue.