Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Synthesis of Indazolones via Friedel–Crafts Cyclization of Blocked (Masked) N-Isocyanates
André M. Beauchemin, Eslam B. Elkaeed, Jing An
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01607

DOI: 10.1021/acs.joc.7b01607

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