EnglishA 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.
| Data di pubblicazione: | 2014 |
| Titolo: | Ring opening of heterocycles containing a C–N double bond: a simple synthesis of imides promoted by acyl palladium species |
| Autore/i: | Perrone, Serena; Cannazza, Giuseppe; Caroli, Antonio; Salomone, Antonio; Troisi, Luigino |
| Autore/i UNIMORE: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tet.2014.07.099 |
| Rivista: | |
| Volume: | 70 |
| Pagina iniziale: | 6938 |
| Pagina finale: | 6943 |
| Codice identificativo ISI: | WOS:000341550600003 |
| Codice identificativo Scopus: | 2-s2.0-84923650069 |
| Citazione: | 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. |
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