106782-17-6Relevant articles and documents
Preparation of the maleic anhydride nucleus from dichloro γ-lactams: Focus on the role of the N-substituent in the functional rearrangement and in the hydrolytic steps
Ghelfi, Franco,Pattarozzi, Mariella,Roncaglia, Fabrizio,Parsons, Andrew F.,Felluga, Fulvia,Pagnoni, Ugo M.,Valentin, Ennio,Mucci, Adele,Bellesia, Franco
, p. 3131 - 3141 (2008)
The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro γ-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide. Georg Thieme Verlag Stuttgart.
