Synthesis of Sulfonamide Derivatives of Carboranyl Porphyrins Based on 5-(4-Aminophenyl)-10,15,20-triphenylporphyrin and Mercapto Carboranes

Valentina A. Ol’shevskaya,^a@ Viktoriya M. Alpatova,^b Nadejda V. Konovalova,^b Elena G. Kononova,^a Yurii A. Borisov,^a Evgeny G. Rys,^a Elena S. Kolotova,^сand Aleksander A. Shtil^с

^aA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation

^bMoscow Technological University, M.V. Lomonosov Institute of Fine Chemical Technologies, 119571 Moscow, Russian Federation

^сN.N. Blokhin National Medical Center of Oncology, 115478 Moscow, Russian Federation

^@Corresponding author E-mail: olshevsk@ineos.ac.ru

DOI: 10.6060/mhc180277o
Macroheterocycles 2018 11(3) 251-256

New carboranyl substituted sulfonamide porphyrins were synthesized in good yields by the reaction of amino group of 5-(p-aminophenyl)-10,15,20-triphenylporphyrin with carboranylsulfonyl chlorides prepared in situ by oxidative chlorination of corresponding mercapto carborane with trichloroisocyanuric acid in MeCN–H₂O system. The reactions were carried out under mild conditions. The structure of all compounds obtained was confirmed by means of electronic, IR, ¹Н and ¹¹B NMR spectroscopy and mass spectrometry. Quantum-chemical studies by DFT calculations were carried out for synthesized porphyrin derivatives.

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Synthesis of Sulfonamide Derivatives of Carboranyl Porphyrins Based on 5-(4-Aminophenyl)-10,15,20-triphenylporphyrin and Mercapto Carboranes

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