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Exo ring opening in methyl pheophorbide a 132-amide derivatives under the action of amines

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Abstract

A reaction of methyl pheophorbide a 132-amide derivatives with amines was studied to explore a possibility of using this reaction in the synthesis of new macrocyclic compounds. It was shown that the exo ring opening can be realized, however, the yields of the corresponding derivatives are lower than in the case of parent methyl pheophorbide a. It can be explained by decreased reactivity of the exo ring in methyl pheophorbide a 132-amide derivatives due to the steric hindrance arising during the formation of the sp3-hybridized intermediate when an amine molecule attacks the carbonyl carbon atom of the exo ring and, to a lesser extent, by decreased partial positive charge on this carbon atom due to the smaller negative inductive effect of the amide group as compared to the ester one.

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Authors and Affiliations

  1. P. Sorokin Syktyvkar State University, 55 Octyabr’skii prosp., 167001, Syktyvkar, Russian Federation

    L. A. Tulaeva, E. I. Pushkareva & O. V. Tolstikova

  2. Institute of Chemistry, Komi Scientific Centre, Ural Branch of the Russian Academy of Sciences, 48 ul. Pervomaiskaya, 167000, Syktyvkar, Russian Federation

    D. V. Belykh

Authors
  1. L. A. Tulaeva
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  2. E. I. Pushkareva
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  3. O. V. Tolstikova
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  4. D. V. Belykh
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Correspondence to L. A. Tulaeva or D. V. Belykh.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 359–368, February, 2021.

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Tulaeva, L.A., Pushkareva, E.I., Tolstikova, O.V. et al. Exo ring opening in methyl pheophorbide a 132-amide derivatives under the action of amines. Russ Chem Bull 70, 359–368 (2021). https://doi.org/10.1007/s11172-021-3093-7

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