ISSN 1070-3632, Russian Journal of General Chemistry, 2012, Vol. 82, No. 3, pp. 413–416. © Pleiades Publishing, Ltd., 2012.
Original Russian Text © E.A. Dikusar, V.I. Potkin, 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. 3, pp. 420–423.
413
Synthesis of o(m)-Carborane-Containing Azomethines
E. A. Dikusar
a,b
, V. I. Potkin
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 of 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 of National Academy of Sciences of Belarus, Minsk, Belarus
Received January 18, 2011
Abstract—A method of preparative synthesis of o(m)-carborane-containing azomethines via the condensation
of о(m)-carboranyl-С-methylene-4-formylbenzoates with aliphatic, cycloaliphatic, and aromatic amines was
developed.
Previously we have reported on the synthesis of
o(m)-carborane-containing Schiff bases via the con-
densation of vanillin esters of o(m)-carborane-C-car-
boxylic acid and vanillin with amines [1–4]. The car-
borane nitrogen-containing derivatives are of interest
for research in the field of the boron neutron capture
DOI: 10.1134/S1070363212030085
IIIа, IIIb
CHO
H
2
NR
IVа−IVz', Vа−Vz'
C(O)OCH
2
CB
10
H
10
CH-o(m)
C
C(O)OCH
2
CB
10
H
10
CH-o(m)
H N
R
o(m)-HCB
10
H
10
CCH
2
OH
4-HC(O)C
6
H
4
C(O)Cl, Py
−Py HCl
Iа, Ib
IVy', IVz', Vy', Vz'
HC
N
C(O)CB
10
H
10
CH-o(m)
2
IVx', Vx'
HC
N(CH
2
)
3
C(O)CB
10
H
10
CH-o(m)
2
IVy, Vy
Me N
O
H
Iа, IIIа, IVа– IVz' are о-carborane derivatives; Ib, IIIb, Vа–Vz' are m-carborane derivatives; IV, V: R = n-C
16
H
33
(a), n-
C
18
H
37
(b), cyclo-С
6
H
11
(c), СH(1-Ad)Me (d), L-CH(CHMe
2
)CO
2
Me (e), L-CH(CHCH
2
Me
2
)CO
2
Me (f), L-CH(CHMeEt)
CO
2
Me (g), L-CH(CH
2
Ph)CO
2
Me (h), 4-MeC
6
H
4
(i), 2-biphenyl (j), 4-biphenyl (k), 1-naphthyl (l), 2-naphthyl (m), 3-
BrC
6
H
4
(n), 4-BrC
6
H
4
(o), 4-IC
6
H
4
(p), 1-bromo-2-naphthyl (q), 2-hydroxyphenyl (r), 4-phenoxyphenyl (s), 4-EtC(O)C
6
H
4
(t), 3-HO
2
CC
6
H
4
(u), 4-HO
2
CC
6
H
4
(v), 4-EtO
2
CC
6
H
4
(w), 4-BuO
2
CC
6
H
4
(x); IVx', Vx' are 1,6-hexamethylene diamine
derivatives; IVy', IVz' , Vy', Vz' are 1,3- and 1,4-phenylene diamine derivatives.
therapy of the tumor diseases, radionuclide diagnostics
and therapy [5, 6].
In this work we describe the method of preparative
synthesis of new o(m)-carborane azomethines IVa–
IVz' and Va–IVz' by the condensation of o(m)-