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Synthesis of purpurin-18 imide derivatives from chlorophyll-a and -b by modifications and functionalizations along their peripheries

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Abstract

The methyl pheophorbide-a and methyl pheophorbide-b were used as starting materials and converted to purpurin-18 ester by ring-opening and rearrangement reaction in their exocyclic ring. N-Substituted purpurin-18 imides were obtained from purpurin-18 ester through amidation reaction of six-membered cyclic anhydride. Further chemical modifications along their peripheries were carried out by a variety of common reactions, including electrophilic substitution, Wittig reaction, allomerization and Vilsmeier reaction, to afford the title compounds with long-wavelength absorption. The structures of all new chlorins were characterized by elemental analysis, IR, UV–vis and 1H NMR spectra.

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Acknowledgments

This work was supported by the National Natural Science Foundations of China (No. 21272048) and the Natural Science Foundation of Shandong Province of China (No. Y2008B49).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Yantai University, Yantai, 264005, People’s Republic of China

    J. J. Wang, Y. F. Yin & Z. Yang

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  1. J. J. Wang
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  2. Y. F. Yin
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  3. Z. Yang
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Correspondence to J. J. Wang.

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Wang, J.J., Yin, Y.F. & Yang, Z. Synthesis of purpurin-18 imide derivatives from chlorophyll-a and -b by modifications and functionalizations along their peripheries. J IRAN CHEM SOC 10, 583–591 (2013). https://doi.org/10.1007/s13738-012-0194-0

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  • DOI: https://doi.org/10.1007/s13738-012-0194-0

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