Site-Selective Modification of a Porpholactone-Selective Synthesis of 12,13-and 17,18-Dihydroporpholactones

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.

keywords

1,3-DIPOLAR CYCLOADDITION REACTIONS; MESO-TETRAARYLPORPHYRINS; FREE-BASE; PORPHYRIN; BETA; CHLORIN; RING; TETRAARYLCHLORINS; CHLOROLACTAMS; REACTIVITY

subject category

Biochemistry & Molecular Biology; Chemistry

authors

Cerqueira, AFR; Snarskis, G; Zurauskas, J; Guieu, S; Paz, FAA; Tome, AC

our authors

acknowledgements

This research was funded by Fundacao para a Ciencia e a Tecnologia (FCT), through project PTDC/QEQ-QOR/6160/2014 and research units UID/QUI/00062/2019, UIDB/50006/2020, and UIDB/50011/2020.

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