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. Author manuscript; available in PMC: 2021 Mar 30.
Published in final edited form as: J Am Chem Soc. 2020 Jan 14;142(4):1987–1994. doi: 10.1021/jacs.9b11566

Scheme 1. Synthesis of the Naphthyridine-Containing Tetrapyrrole 7a.

Scheme 1.

aReagents, conditions, and yields: (a) Pd(OAc)2, PPh3, K2CO3, DMF/H2O, N2, reflux, 24 h (yield: 70%); (b) NaOH, EtOH/H2O, 85 °C, 5 h (yield 95%); (c) ethylene glycol, 185 °C, 50 min (yield: 91%); (d) I2/KI, NaHCO3, CH2Cl2/H2O, rt, 1 h, Na2S2O3 (yield: 65%); (e) Pd(PPh3)4, K2CO3, DMF/H2O, reflux, 16 h (yield: 45%).