Opening of Exocycle of the Methyl Pheophorbide a 13(2)-Amide Derivatives in a Water-Acetone Solution in the Presence Hydrochloric Acid

D. V. Belykh,^@ and I. S. Khudyaeva

Federal State Budget Organization of Science Institute of Chemistry, Komi Science Centre, Ural Division RAS, 167000 Syktyvkar, Russia

^@Corresponding author E-mail: belykh-dv@mail.ru

DOI: 10.6060/mhc171039b
Macroheterocycles 2018 11(3) 273-276

It has been shown that under the action of water on methyl pheophorbide a 13(2)-amide derivatives in acidic conditions (mixture of concentrated hydrochloric acid and acetone), in addition to hydrolyzing of the ester group of the substituent at position 17, exocycle opening with the formation of the corresponding chlorin e₆ 15-amide derivatives occurs. The possibility of exocycle opening seems to be caused by its strength due to the presence of a relatively bulky amide substituent, as well as to the protonation of the amide group, which facilitates the rupture of the C(13(1))-C(13(2)) bond.

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Opening of Exocycle of the Methyl Pheophorbide a 13(2)-Amide Derivatives in a Water-Acetone Solution in the Presence Hydrochloric Acid

References: