Tetrahedron, 2015 (71) 1940-1951

A.V. Galenko, A.F. Khlebnikov, M.S. Novikov, M.S. Avdontseva

“Synthesis of 3-(1,2-dioxoethyl)- and 2,3-dicarbonyl-containing pyrroles”

Tetrahedron, 2015, 71, 1940-1951

The transition metal-catalyzed reaction of 2H-azirines with 1,2,4-tricarbonyl compounds leads to 3-(1,2-dioxoethyl)- and 2,3-dicarbonyl-pyrrole derivatives, useful building blocks for the preparation of 3-heterocyclyl pyrroles and pyrroles fused with heterocycles. The influence of catalysts and the reaction conditions on the yields of pyrroles and the regioselectivity of the reaction were studied. Experimental and theoretical results suggest that the reaction proceeds via the formation of an intermediate azirine–metal complex and subsequent nucleophilic N–C3 bond cleavage.

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