Chemistry of Heterocyclic Compounds, Vol. 44, No. 5, 2008
ON THE SYNTHESIS OF THE FIRST
REPRESENTATIVES OF BIS(BENZO)-
BISPIDINOAZA-14-CROWN-4 ETHERS
A. I. Komarova
1
, A. N. Levov
2
, A. T. Soldatenkov
2
, and S. A. Soldatova
2
Keywords: bis(benzo)bispidinoaza-14-crown-4-ethers, condensation with aromatic aldehydes and
ammonia.
In previous work [1-3], we reported the first syntheses of dibenzoazacrown ethers containing a
constituent γ-piperidone fragment in the macrocycle. This success led us to consider the possibility of using
these compounds for the construction of a new, more complicated heterocyclic system containing a bispidine
fragment in the crown ether part of the macrocycle. Hence, we studied the condensation of azacrownophane 1
[3] with aromatic aldehydes 2a,b and ammonium acetate. Maintenance of this mixture in a solution of ethanol
and acetic acid for seven days at 20°C followed by crystallization gave compounds 3a in 15% yield and 3b in
11% yield. These azacrown ethers belong to a new group of lariat ethers [4], in which the constituent
N
H
O
O
O
O
N
H
N
H
O
O
O
O
R
R
+ RCHO + NH
4
OAc
1
2a,b
3a,b
2, 3 a R = 4-FC
6
H
4
, b R = (MeO)
2
C
6
H
3
1
24
23
22
21
21
22
1
23
24
2
3
4
5
6
7
9
10 12
13
15
16
17
18
19
20
3,7-diazabicyclo[3.3.1]nonane fragment has additional sites for coordination with metal cations. These sites are
auxiliary upon cooperation with the crown ether part of the molecule. Furthermore, the functionality of this
fragment may lead to derivatives of this new heterocyclic system with enhanced potential for biological activity
since, as predicted by the PASS Internet program [5], 3a,b may display cardioprotective (69-76%) and
antineoplastic activity (62-68%).
__________________________________________________________________________________________
1
D. Mendeleev University of Chemical Technology of Russia, Moscow 125047, Russia; e-mail:
alexkom18@yandex.ru.
2
Russian Peoples' Friendship University, Moscow 117198, Russia; e-mail:
asoldatenkov@mail.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 784-786,
May, 2008. Original article submitted March 18, 2008.
624 0009-3122/08/4405-0624©2008 Springer Science+Business Media, Inc.