Журнал "Макрогетероциклы"

D. V. Belykh,^a@ I. S. Khudyaeva,^a O. M. Startceva,^a I. V. Gruzdev,^b and Y. V. Romanenko^c

^aInstitute of Chemistry of Komi Scientific Centre of Ural Division of Russian Academy of Sciences, 167982 Syktyvkar, Russia

^bInstitute of Biology of Komi Scientific Centre of Ural Division of Russian Academy of Sciences, 167982 Syktyvkar, Russia

^cInstitute of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

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

DOI: 10.6060/mhc160540b

Macroheterocycles 2016 9(4) 366-372

In order to develop new methods of chlorophyll derivatives chemical modification for synthesis of new biologically active compounds we studied aminomethylation of nickel complexes of chlorophyll a derivatives by action of dimethylmethyleneammonium iodide (“Eschenmoser’s reagent”), and bis(N,N-dimethylamino)methane. It has been shown that under the action of dimethylmethyleneammonium iodide the insertion of one dimethylaminomethyl substituent into vinyl group occurs, and the action of bis(N,N-dimethylamino)methane leads to the introduction of two dimethylaminomethyl substituents into vinyl group. An attempt to carry out the reaction of monoaminomethilated derivatives with bis(N,N-dimethylamino)methane does not lead to the insertion of the second dimethylaminomethyl group. This suggests that the first dimethylaminomethyl group is introduced at position 3(1) under the action of bis(N,N-dimethylamino)methane. The reaction with exocycle to form the corresponding 13(2)-derivatives is possible in addition to vinyl group aminomethylation.

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