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. 2021 Dec 1;122(1):565–788. doi: 10.1021/acs.chemrev.1c00449

Scheme 385. Shape-Persistent Macrocycles Containing peri-Condensed Pyridine Rings.

Scheme 385

Reagents and conditions: (a)755 AIBN, NBS (2.5 equiv), CCl4, 77 °C, 5 h; (b) Na2CO3, 1,4-dioxane, 80 °C, 14 h; (c) TFA (10 equiv), dichloroethane, 70 °C, 18 h; (d) n-butyl vinyl ether (10 equiv), MeCN, 45 °C, 25 h; (e) n-butyl vinyl ether (10 equiv), degassed CH3CN, rt; (f) air; (g) 2,3-dihydrofuran (50 equiv), MeOH, 25 °C, 24 h; (h) nBuLi, THF, −78 to 25 °C, 16 h.