Site-Selective Modification of a Porpholactone-Selective Synthesis of 12,13-and 17,18-Dihydroporpholactones
authors Cerqueira, AFR; Snarskis, G; Zurauskas, J; Guieu, S; Paz, FAA; Tome, AC
nationality International
journal MOLECULES
author keywords porpholactones; dihydroporpholactones; 1; 3-dipolar cycloadditions; pyrrolidines; isoxazolidines
keywords 1,3-DIPOLAR CYCLOADDITION REACTIONS; MESO-TETRAARYLPORPHYRINS; FREE-BASE; PORPHYRIN; BETA; CHLORIN; RING; TETRAARYLCHLORINS; CHLOROLACTAMS; REACTIVITY
abstract The reaction of meso-tetrakis(pentafluorophenyl)porpholactone with azomethine ylides and nitrones affords pyrrolidine-fused and isoxazolidine-fused dihydroporpholactones that display, respectively, isobacteriochlorin- and chlorin-type UV-Vis spectra. These reactions are site-selective, yielding, respectively, 17,18- or 12,13-dihydroporpholactones. The crystal and molecular features of pyrrolidine-fused and isoxazolidine-fused dihydroporpholactones were unveiled from single-crystal X-ray diffraction studies.
publisher MDPI
year published 2020
volume 25
issue 11
digital object identifier (doi) 10.3390/molecules25112642
web of science category Biochemistry & Molecular Biology; Chemistry, Multidisciplinary
subject category Biochemistry & Molecular Biology; Chemistry
unique article identifier WOS:000553858800179
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journal impact factor 3.267
5 year journal impact factor 3.589
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