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

[ Vol. 10 , Issue. 3 ]

Author(s):

Orazio A. Attanasi, Luca Bianchi, Jure Bezensek, Gianfranco Favi, Gianluca Giorgi, Fabio Mantellini, Branko Stanovnik and Jurij Svete   Pages 472 - 480 ( 9 )

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.

Keywords:

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

Affiliation:

Istituto di Chimica Organica, Università degli Studi di Urbino “Carlo Bo”, Via I Maggetti, 24, 61029 Urbino (PU), Italy.



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