Russian Chemical Bulletin, International Edition, Vol. 66, No. 11, pp. 2126—2130, November, 2017
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2126—2130, November, 2017.
10665285/17/66112126 © 2017 Springer Science+Business Media, Inc.
Synthesis of Nsubstituted imidazo[4,5e]benzo[1,2c;3,4c
V. L. Korolev,
V. V. Toporov,
N. L. Merkulova,
V. M. Danilenko,
V. P. Ivshin,
and T. S. Pivina
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
47 Leninsky prosp., 119991 Moscow, Russian Federation.
Fax: +7 (499) 135 5328. Email: email@example.com; firstname.lastname@example.org; email@example.com
Mari State University,
1 pl. Lenina, 424000 YoshkarOla, Russian Federation.
Fax: +7 (836) 264 1541
Lyceum and Gymnasium Complex in the SouthEast,
32 Bild. 6 ul. Zelenodol´skaya, 109457 Moscow, Russian Federation.
Fax: +7 (495) 362 3440
]difuroxans were synthesized by phase
transfer catalyzed alkylation of imidazo[4,5e]benzo[1,2c;3,4c
]difuroxan salts with vari
ous alkylating agents. Acid hydrolysis of N(ethoxycarbonylmethyl)imidazo[4,5e]benzo
]difuroxans gives the corresponding carboxylic acids. Structures of the synthe
sized compounds were confirmed by NMR spectroscopy, high resolution mass spectrometry,
IR spectroscopy, and elemental anslysis.
Kew words: imidazo[4,5e]benzo[1,2c;3,4c
]difuroxans, alkylation, phase transfer
]difuroxans that are
studied by our
and other research groups
prise two pharmacologically promising fragments, i.e.,
furoxan and benzimidazole moieties. Therefore, these
compounds can be regarded as potential multitarget
drugs. Furoxans are known for their ability to generate
a gasotransmitter that participates in nu
merous biological processes.
A great interest in the phar
macological properties of benzimidazole has been prom
pted by the finding that Nribosyl5,6dimethylbenzimid
azole serves as an axial ligand for cobalt in vitamin B
and this interest is still present.
derivatives were found to exhibit antiparasitic,
macological properties dramatically depend on the nature
of the substituents and their positions in the imidazole
Thus, in continuation of our research on the syn
thesis of imidazo[4,5e]benzo[1,2c;3,4c
seems reasonable to examine the possibility of introduc
ing different substituents to the imidazole nitrogen atom.
In the present work, we describe the synthesis of
new Nsubstituted imidazo[4,5e]benzo[1,2c;3,4c
furoxans by phasetransfer catalyzed alkylation
the salts generated in situ from compounds 1a—c with
halo derivatives of saturated and unsaturated hydrocar
bons, esters and nitriles of carboxylic acids (Scheme 1).
The reactions were carried out in the system solid
)—liquid phase (acetone—triethylamine—
= H (a), Me (b), Et (c)
unds 2 unds 2
a HMe g HCH
b HEt h HCH
c HPr I HCH
d HBu j Me CH
e H nC
k Et CH
f H nC
Reagents and conditions: K
Hal are given in Table 1.
DMSO) for 2—240 h at 20—60
C (Table 1). Dibenzo
18crown6 was used as a phase transfer catalyst.