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Article

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

by
Ana F. R. Cerqueira
1,
Gustautas Snarskis
1,
Jonas Zurauskas
1,
Samuel Guieu
1,2,
Filipe A. Almeida Paz
2 and
Augusto C. Tomé
1,*
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
*
Author to whom correspondence should be addressed.
Molecules 2020, 25(11), 2642; https://doi.org/10.3390/molecules25112642
Submission received: 20 May 2020 / Revised: 3 June 2020 / Accepted: 4 June 2020 / Published: 6 June 2020
(This article belongs to the Special Issue Exclusive Papers of the Editorial Board Members of the Organic Chemistry Section of Molecules)
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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: porpholactones; dihydroporpholactones; 1,3-dipolar cycloadditions; pyrrolidines; isoxazolidines porpholactones; dihydroporpholactones; 1,3-dipolar cycloadditions; pyrrolidines; isoxazolidines
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MDPI and ACS Style

Cerqueira, A.F.R.; Snarskis, G.; Zurauskas, J.; Guieu, S.; Paz, F.A.A.; Tomé, A.C. Site-Selective Modification of a Porpholactone—Selective Synthesis of 12,13- and 17,18-Dihydroporpholactones. Molecules 2020, 25, 2642. https://doi.org/10.3390/molecules25112642

AMA Style

Cerqueira AFR, Snarskis G, Zurauskas J, Guieu S, Paz FAA, Tomé AC. Site-Selective Modification of a Porpholactone—Selective Synthesis of 12,13- and 17,18-Dihydroporpholactones. Molecules. 2020; 25(11):2642. https://doi.org/10.3390/molecules25112642

Chicago/Turabian Style

Cerqueira, Ana F. R., Gustautas Snarskis, Jonas Zurauskas, Samuel Guieu, Filipe A. Almeida Paz, and Augusto C. Tomé. 2020. "Site-Selective Modification of a Porpholactone—Selective Synthesis of 12,13- and 17,18-Dihydroporpholactones" Molecules 25, no. 11: 2642. https://doi.org/10.3390/molecules25112642

APA Style

Cerqueira, A. F. R., Snarskis, G., Zurauskas, J., Guieu, S., Paz, F. A. A., & Tomé, A. C. (2020). Site-Selective Modification of a Porpholactone—Selective Synthesis of 12,13- and 17,18-Dihydroporpholactones. Molecules, 25(11), 2642. https://doi.org/10.3390/molecules25112642

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