Divergent C–H activation synthesis of chalcones, quinolones and indoles

Abstract

We here report a condition-controlled divergent synthesis strategy of chalcones, quinolones and indoles, which was achieved via a C–H activation reaction of N-nitrosoanilines and cyclopropenones.

Recent Advances and Strategies for the Transition‐Metal‐Catalyzed C−H Functionalization of N‐Nitrosoanilines

“…Shi and co‐workers explored a novel Rh(III)‐catalyzed C−H functionalization of N ‐nitrosoanilines using cyclopropenones to form chalcones, quinolines, and indoles under controlled reaction conditions (Scheme 30). [32] Activation of the C−H bond of N ‐nitrosoanilines was envisioned to allow the insertion of cyclopropenones, giving rise to chalcone moieties, which possibly undergo a [3+3] annulation reaction to form quinolones. Different rhodium catalysts and additives were screened to optimize the reaction conditions along with variations in temperature and time.…”

Recent advances in the synthesis of indoles via C–H activation aided by N–N and N–S cleavage in the directing group

“…A cyclisation involving N ‐nitrosoanilines ( 89 ) and cyclopropenones ( 90 ) under Rh(I) and Rh(III) co‐catalysts successfully affords indoles ( 91 ) in excellent yields (Scheme 27 ) . [ 39 ]…”

Synthetic Applications of Cyclopropene and Cyclopropenone: Recent Progress and Developments

“…A plausible mechanism is shown in Scheme 63. [125] Silylanalogous of drug molecules generally enhances bioactivity and sometimes reduces toxicity or repurpose the drug. (Benzo)suberones, (benzo)oxepinones, and their derivatives are prevalent in various marketed drugs and natural products and also widely used as synthetic key intermediates.…”