Transition-Metal-Free, Atom- and Step-Economic Synthesis of Aminoketopyrrolizines from Benzylamine, Acylethynylpyrroles, and Acylacetylenes.
A concise, atom-economic strategy for the synthesis of pyrrolizines with amino and keto substituents has been developed. It includes the following key steps: (i) the base-catalyzed (K3PO4/DMSO) addition of a benzylamine to 2-acylethynylpyrroles and (ii) noncatalyzed addition of enaminones obtained to the triple bond of acylacetylenes followed by intramolecular cyclization of the intermediate pentadiendiones thus formed to the target 1-(benzylamino)-2-acyl-3-methylenoacylpyrrolizines.
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky Str, 664033 Irkutsk, Russian Federation.
Lyubov' N
LN
Sobenina
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky Str, 664033 Irkutsk, Russian Federation.
Denis N
DN
Tomilin
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky Str, 664033 Irkutsk, Russian Federation.
Elena F
EF
Sagitova
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky Str, 664033 Irkutsk, Russian Federation.
Igor' A
IA
Ushakov
A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences , 1 Favorsky Str, 664033 Irkutsk, Russian Federation.
Boris A
0000-0002-0430-3215
BA
Trofimov