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Synthesis of Indazolones via Friedel–Crafts Cyclization of Blocked (Masked) N‑Isocyanates

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journal contribution
posted on 22.08.2017, 00:00 by Eslam B. Elkaeed, Jing An, André M. Beauchemin
Nitrogen-substituted isocyanates (N-isocyanates) are rare amphoteric reagents with high, but underdeveloped synthetic potential. Herein, we study the formation of indazolones by Friedel–Crafts cyclization of N-isocyanates using blocked (masked) N-isocyanate precursors: the effect of the masking group and the reaction scope have been delineated. Substrate synthesis has also been improved using a reported copper-catalyzed coupling of arylbismuth­(V) reagents that is compatible with the hemilabile OPh blocking group.