ISSN 1070-3632, Russian Journal of General Chemistry, 2012, Vol. 82, No. 6, pp. 1069–1072. © Pleiades Publishing, Ltd., 2012. Original Russian Text © E.A. Dikusar, V.I. Potkin, N.G. Kozlov, D.A. Rudakov, T.D. Zvereva, S.K. Petkevich, M.M. Ogorodnikova, A.P. Yuvchenko, M.P. Bei, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 6, pp. 910–913. 1069 Synthesis of Azomethines Based on 4-Formylphenyl m-Carboranyl-C-methanoate E. A. Dikusar a,b , V. I. Potkin a , N. G. Kozlov a , D. A. Rudakov a , T. D. Zvereva a , S. K. Petkevich a , M. M. Ogorodnikova a , A. P. Yuvchenko b , and M. P. Bei b a Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072 Belarus e-mail: dikusar@ifoch.bas-net.by b Institute of Chemistry of New Materials, National Academy of Sciences of Belarus, Minsk, Belarus Received April 25, 2011 Abstract—A preparative method for the synthesis of m-carborane azomethines via the condensation of m- carborane-C-4-formylphenyl methanoate with aliphatic, cycloaliphatic, and aromatic amines was developed. Previously a synthesis has been reported of o(m)- carborane-containing azomethines starting from o(m)- carboranyl-C-methylene-4-formyl benzoates [1]. The nitrogen-containing carborane derivatives are of interest as the agents in the boron neutron capture therapy of the neoplastic diseases, radionuclide dia- gnostics and therapy [2, 3]. In this work we describe a method of the preparative synthesis of new m-carborane azomethines V via the condensation of 4-formylphenyl m-carboranyl-C-metha- noate III with aliphatic, cycloaliphatic, and aromatic amines IV. The yield of compounds V was 85–89%. The starting 4-formylphenyl m-carboranyl-C-methanoate III was synthesized by the esterification of 4- formylmethanol I with m-carboranyl-C-carboxylic acid chloride II in the presence of pyridine in 91% yield. The resulting carborane derivatives III, Va–Vz are crystalline or amorphous glassy substances, soluble in Et 2 O, DMF, DMSO, and CHCl 3 . The composition of compounds III and V was proved by the elemental analysis and molecular weight determination (see the table), the structure, by spectral methods. DOI: 10.1134/S1070363212060059 V, R = n-C 18 H 37 (a), СH(1-Ad)Me (b), L-CH(CHMe 2 )CO 2 Me (c), L-CH(CHCH 2 Me 2 )CO 2 Me (d), L-CH(CHMeEt)CO 2 Me (e), C 6 H 5 (f), 4-MeC 6 H 4 (g), 2-biphenyl (h), 4-biphenyl (i), 1-naphthyl (j), 2-naphthyl (k), 4-FC 6 H 4 (l), 3-BrC 6 H 4 (m), 4-BrC 6 H 4 (n), 4-IC 6 H 4 (o), 1-bromo-2-naphthyl (p), 2-hydroxyphenyl (q), 4-ethoxyphenyl (r), 4-phenoxyphenyl (s), 4-MeC(O)C 6 H 4 (t), 4-EtC(O)C 6 H 4 (u), C 6 H 4 -3-COOH (v), C 6 H 4 -4-COOH (w), C 6 H 4 -4-COOEt (x), C 6 H 4 -4-COOBu (y), (z). N O Vа-Vz III CHO OH C C CCl O CHO O C HC C O HC O C HC C O NR I II + H Py Py HCl RNH 2 IV