Literature DB >> 12509880

Free base meso-tetraaryl-morpholinochlorins and porpholactone from meso-tetraaryl-2,3-dihydroxy-chlorin.

Jason R McCarthy1, Hilary A Jenkins, Christian Brückner.   

Abstract

meso-Tetraaryl-2,3-dihydroxychlorins (1) were converted in one step to the novel free base macrocycles meso-tetraaryl-2,3-dialkoxy-2a-oxa-2a-homoporphyrins (morpholinochlorins, 3). Their bathochromically shifted chlorin-type UV-vis spectra indicate the presence of a nonplanar chromophore. The structure of meso-tetratolyldiethoxymorpholinochlorin (3b), as determined by X-ray crystallography, was found to be largely planar, suggesting significant conformational flexibility of these macrocycles. Oxidation of diol 1 with MnO(4)(-) generates known porpholactone 4 in high yields. [reaction--see text]

Entities:  

Year:  2003        PMID： 12509880     DOI： 10.1021/ol027072a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  meso-arylporpholactones and their reduction products.

Authors:  Christian Brückner; Junichi Ogikubo; Jason R McCarthy; Joshua Akhigbe; Michael A Hyland; Pedro Daddario; Jill L Worlinsky; Matthias Zeller; James T Engle; Christopher J Ziegler; Matthew J Ranaghan; Megan N Sandberg; Robert R Birge
Journal:  J Org Chem       Date:  2012-07-19       Impact factor: 4.354

2.  Erratum to: Axial imidazole binding strengths in porphyrinoid cobalt(III) complexes as studied by tandem mass spectrometry.

Authors:  Ekta Mishra; Jill L Worlinsky; Thomas M Gilbert; Christian Brückner; Victor Ryzhov
Journal:  J Am Soc Mass Spectrom       Date:  2012-06-12       Impact factor: 3.109

3.  Axial imidazole binding strengths in porphyrinoid cobalt(III) complexes as studied by tandem mass spectrometry.

Authors:  Ekta Mishra; Jill L Worlinsky; Thomas M Gilbert; Christian Brückner; Victor Ryzhov
Journal:  J Am Soc Mass Spectrom       Date:  2012-04-12       Impact factor: 3.109

4.  Stepwise conversion of two pyrrole moieties of octaethylporphyrin to pyridin-3-ones: synthesis, mass spectral, and photophysical properties of mono and bis(oxypyri)porphyrins.

Authors:  Claudia Ryppa; Dariusz Niedzwiedzki; Nicole L Morozowich; Rapole Srikanth; Matthias Zeller; Harry A Frank; Christian Brückner
Journal:  Chemistry       Date:  2009-06-02       Impact factor: 5.236

5.  MS/MS fragmentation behavior study of meso-phenylporphyrinoids containing nonpyrrolic heterocycles and meso-thienyl-substituted porphyrins.

Authors:  Ekta Mishra; Jill L Worlinsky; Christian Brückner; Victor Ryzhov
Journal:  J Am Soc Mass Spectrom       Date:  2013-10-18       Impact factor: 3.109

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

Authors:  Ana F R Cerqueira; Gustautas Snarskis; Jonas Zurauskas; Samuel Guieu; Filipe A Almeida Paz; Augusto C Tomé
Journal:  Molecules       Date:  2020-06-06       Impact factor: 4.411

7.  Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes.

Authors:  Damaris Thuita; Dinusha Damunupola; Christian Brückner
Journal:  Molecules       Date:  2020-09-22       Impact factor: 4.411
  7 in total

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