A synthesis of fuctionalized 2-amino-3-cyano pyrroles from terminal alkynes, sulfonyl azides and phenacylmalononitriles

Abstract

A copper-catalyzed synthesis of functionalized 2-amino-3-cyanopyrroles via interception of the reactive N-sulfonoketenimines, generated in situ from terminal alkynes and sulfonyl azides, by phenacylmalononitriles in the presence of copper(I) iodide and...

Multicomponent cyclization with azides to synthesize N-heterocycles

“…Triazoles can also be precursors of enamines. In 2022, a new strategy for the construction of functionalized 2-amino-3-cyano pyrroles 69 was developed by Akbarzadeh et al 55 The reactions consisted of a copper-catalyzed azide–alkyne cycloaddition reaction; this involved the combination of terminal alkynes and sulfonyl azides followed by the generation of N -sulfonoketenimine intermediates 70 . Different from the formation of metal carbenoids, the combination of reactive ketenimines with phenacylmalononitriles 71 in the presence of copper( i ) iodide and Et 3 N resulted in the attainment of the anticipated products.…”

Synthesis of pyrrolidin-2-ylidenes and pyrrol-2-ylidenes via 1,3-dipolar cycloaddition of H-bond-assisted azomethine ylides to nitrostyrenes

“…In continuation of our studies on pyrrole synthesis, 21 we developed a method to synthesize highly substituted pyrrolidin-2-ylidene derivatives. These transformations are accessible under mild reaction conditions with readily available precursors.…”