A novel protocol for the synthesis of unsymmetrical indigo-like (E)-α-amino enaminones by rhodium-catalyzed transformations of isatins with 1-tosyl-1,2,3-triazoles has been developed. A plausible reaction mechanism is proposed to account for the formation of structurally important unsymmetrical indigo analogues, which represents a new strategy for C-C bond formation based on the transformations of secondary amides and rhodium azavinylcarbenes.

A cascade reaction of rhodium azavinylcarbenes with Morita-Baylis-Hillman (MBH) adducts enables a novel synthetic approach to 3,4-fused pyrroles. The cascade reaction begins with the insertion of O-H bond into rhodium azavinylcarbenes, subsquent sigmatropic rearrangement provides substituted α,β-unsaturated cyclic ketone intermediates. Then the intramolecular aza Michael addition/oxidative aromatization sequence give rise to a wide range of 3,4-fused pyrroles in good yields, and with excellent functional group compatibility.

No abstract

No abstract

Die Dinitrotoluole (I) werden durch Ethylmercaptid in selektiver Weise zu den Thioethern (II) substituiert.