Reactivity of tetrapyrrolyl nitrones towards dipolarophiles bearing electron-withdrawing groups. Issue 22 (27th May 2015)

• Record Type: Journal Article
• Authors: da Silva, A. Filipa F.; Barata, Joana F.B.; Silva, Ana M.G.; Neves, M. Graça P.M.S.; Tomé, Augusto C.; Silva, Artur M.S.; Cavaleiro, José A.S.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 22(2015)
• Page Start: 2878
• Page End: 2881
• Publication Date: 2015-05-27
• Subjects: Nitrones -- Porphyrinyl nitrones -- Corrolyl nitrones -- 1, 3-Dipolar cycloaddition -- Isoxazolidine derivatives; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.04.066
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The reactivity of porphyrinyl and corrolyl nitrones towards dipolarophiles bearing electron-withdrawing groups was studied and it was found that the two nitrones behave differently in 1, 3-dipolar cycloaddition reactions. While porphyrinyl nitrone reacts with dimethyl fumarate, dimethyl acetylenedicarboxylate and ethyl propiolate to afford the expected isoxazolidine and isoxazoline cycloadducts, the corrolyl nitrone reacts with dimethyl fumarate to provide an isoxazolidine-substituted corrole but with dimethyl acetylenedicarboxylate it gives amide derivatives.