An efficient and highly stereoselective approach for the C3 functionalization of indolizines through rhodium (II)-catalyzed insertion of aza-vinyl carbenes to synthesize Nsulfonylamine alkenyl derivatives of indolizines is disclosed. Variably functionalized indolizines underwent C3 functionalization to afford moderate to good yields. Under similar reaction conditions pyrrolo[1,2-a]quinolines resulted in regioselective C1 functionalization to give their N-sulfonylamine alkenyl derivatives. The reaction methodology was successfully extended for the preparation of 1,3-bis(Nsulfonylamine alkenyl)indolizine derivatives and C3-functionalized indolizines were used for the preparation of new molecular entities.[a] N. . Synthesis of 1,3-bis-N-sulfonylamine alkenyl derivatives of indolizines.
Scheme 4. Synthetic applications of C3 functionalised indolizines.Scheme 5. Plausible mechanism of C3 functionalization of indolizine.
Copper sulfate catalyzed an efficient, inexpensive, and environment-friendly protocol that has been developed for N-arylation of amines with 1,3-cyclohexadione-derived aryliodonium ylides in water as a green solvent. Aromatic primary amines substituted with electron-donating as well as electron-withdrawing groups on the aryl ring reacted smoothly with iodonium ylides to give the corresponding diarylamines with good to excellent yields. Also, secondary amines underwent N-arylation to deliver tertiary amines with moderate yields.
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