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

Ana F R Cerqueira; Gustautas Snarskis; Jonas Zurauskas; Samuel Guieu; Filipe A Almeida Paz; Augusto C Tomé

doi:10.3390/molecules25112642

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

Molecules. 2020 Jun 6;25(11):2642. doi: 10.3390/molecules25112642.

Authors

Ana F R Cerqueira¹, Gustautas Snarskis¹, Jonas Zurauskas¹, Samuel Guieu^{1

2}, Filipe A Almeida Paz², Augusto C Tomé¹

Affiliations

¹ LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.
² CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.

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 cycloadditions; dihydroporpholactones; isoxazolidines; porpholactones; pyrrolidines.

MeSH terms

Isoxazoles / chemistry*
Lactones / chemistry*
Porphyrins / chemistry*
Pyrrolidines / chemistry*
X-Ray Diffraction

Substances

Isoxazoles
Lactones
Porphyrins
Pyrrolidines
pyrrolidine

Grants and funding

PTDC/QEQ-QOR/6160/2014/Fundação para a Ciência e a Tecnologia