A detailed study on the reactivity of various heterocycles, containing a C-N double bond, with acyl palladium species, generated in situ from allyl or benzyl halides and CO, has been performed. While the cyclic imine 2-methyl-1-pyrroline reacted with acyl-palladium intermediates to give a bicyclic β-lactam, other heterocycles containing a C-N double bond conjugated with a heteroatom (O or N), showed a ring-opening reaction leading to functionalized imides with high structural diversity. Such methodology represents a simple and direct way to prepare structurally complex imides. Moreover, a reaction mechanism, involving cationic intermediates, was also proposed.

Ring opening of heterocycles containing a C–N double bond: a simple synthesis of imides promoted by acyl palladium species / Perrone, Serena; Cannazza, Giuseppe; Caroli, Antonio; Salomone, Antonio; Troisi, Luigino. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 70:(2014), pp. 6938-6943. [10.1016/j.tet.2014.07.099]

Ring opening of heterocycles containing a C–N double bond: a simple synthesis of imides promoted by acyl palladium species

CANNAZZA, Giuseppe;
2014

Abstract

A detailed study on the reactivity of various heterocycles, containing a C-N double bond, with acyl palladium species, generated in situ from allyl or benzyl halides and CO, has been performed. While the cyclic imine 2-methyl-1-pyrroline reacted with acyl-palladium intermediates to give a bicyclic β-lactam, other heterocycles containing a C-N double bond conjugated with a heteroatom (O or N), showed a ring-opening reaction leading to functionalized imides with high structural diversity. Such methodology represents a simple and direct way to prepare structurally complex imides. Moreover, a reaction mechanism, involving cationic intermediates, was also proposed.
2014
70
6938
6943
Ring opening of heterocycles containing a C–N double bond: a simple synthesis of imides promoted by acyl palladium species / Perrone, Serena; Cannazza, Giuseppe; Caroli, Antonio; Salomone, Antonio; Troisi, Luigino. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 70:(2014), pp. 6938-6943. [10.1016/j.tet.2014.07.099]
Perrone, Serena; Cannazza, Giuseppe; Caroli, Antonio; Salomone, Antonio; Troisi, Luigino
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1064419
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