Divergent Behavior of the Reactions Between 1,2-Diaza-1,3-dienes and 2,5- Dioxoimidazolidin-4-ylidene-succinates

Title:Divergent Behavior of the Reactions Between 1,2-Diaza-1,3-dienes and 2,5- Dioxoimidazolidin-4-ylidene-succinates

Volume: 10 Issue: 3

Author(s): Orazio A. Attanasi, Luca Bianchi, Jure Bezensek, Gianfranco Favi, Gianluca Giorgi, Fabio Mantellini, Branko Stanovnik and Jurij Svete

Affiliation:

Keywords: Cyclization, 1, 2-Diaza-1, 3-dienes, 2, 5-Dioxoimidazolidin-4-ylidene-succinates, Fused-ring systems, Michael addition, Nitrogen heterocycles.

Abstract: The different base-promoted regioselective reactions between dialkyl (2E,3E)-2-[(dimethylamino)methylene]-3-(1-methyl-2,5- dioxoimidazolidin-4-ylidene)succinates and 1,2-diaza-1,3-dienes are investigated. Under the appropriate reaction conditions it is possible to turn the synthesis towards 1,3-dioxo-2,3,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazoles or 1,3-dioxo-1,2,3,5-tetrahydroimidazo[1,5- a]pyridines. Both these transformations proceed via a double-Michael-addition.

Cite this article as:

A. Attanasi Orazio, Bianchi Luca, Bezensek Jure, Favi Gianfranco, Giorgi Gianluca, Mantellini Fabio, Stanovnik Branko and Svete Jurij, Divergent Behavior of the Reactions Between 1,2-Diaza-1,3-dienes and 2,5- Dioxoimidazolidin-4-ylidene-succinates, Current Organic Synthesis 2013; 10 (3) . https://dx.doi.org/10.2174/1570179411310030009