ISSN 1070-4272, Russian Journal of Applied Chemistry, 2014, Vol. 87, No. 6, pp. 780−786. © Pleiades Publishing, Ltd., 2014.
Original Russian Text © N.G. Kozlov, S.L. Bondarev, Yu.D. Zhikharko, V.N. Knyukshto, R.Z. Lytvyn, Yu.I. Horak, M.D. Obushak, L.I. Basalaeva, 2014, published
in Zhurnal Prikladnoi Khimii, 2014, Vol. 87, No. 6, pp. 775−782.
ORGANIC SYNTHESIS AND INDUSTRIAL
Synthesis, Absorption Spectra, and Luminescence
Properties of Dihydrobenzoacridinone Derivatives
N. G. Kozlov, S. L. Bondarev, Yu. D. Zhikharko, V. N. Knyukshto,
R. Z. Lytvyn, Yu. I. Horak, M. D. Obushak, and L. I. Basalaeva
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
ul. Surganova 13, Minsk, 220072 Belarus
Minsk State Higher Radiotechnical College, pr. Nezavisimosti 62, Minsk, 220005 Belarus
Stepanov Institute of Physics, National Academy of Sciences of Belarus,
pr. Nezavisimosti 68, Minsk, 220005 Belarus
Ivan Franko National University, ul. Sychovych Strel’tsiv 14, Lviv, 79602 Ukraine
Received February 21, 2014
Abstract—9,9-Dimethyl-12-[(5-aryl-2-furyl) (or 5-aryl-2-thienyl, or 5-aryl-1-methyl-1Н-pyrrolyl)]-
7,8,9,10,11,12-hexahydrobenzo[а]acridin-11-ones were synthesized, and their absorption and luminescence
spectrum characteristics in ethanol at room temperature and at 77 K were studied. The spectra suggest the existence
of these compounds in a liquid solution as mixtures of conformers, each of which is characterized by its own
absorption and ﬂ uorescence spectra.
Proceeding with studies on synthesis of organic lumi-
nophores containing carbonyl group , we synthesized
new compounds with the carbonyl group incorporated in
the dihydrobenzoacridine core, following the procedure
that we developed (Scheme 1).
Reﬂ uxing equimolar amounts of 2-naphthylamine I,
appropriate aldehyde IIа–IIf, and dimedone IV in an al-
coholic solution led to selective formation of 9,9-dimeth-
yl-12-[(5-aryl-2-furyl) (or 5-aryl-2-thienyl, or 5-aryl-1-
Dihydrobenzoacridinones Va–Vd can be prepared
both by the reaction of azomethines IIIa–IIId with
2-naphthylamine and by the ternary condensation of
2-naphthylamine, aldehydes IIa–IId, and dimedone IV.
Dihydrobenzoacridinones Ve and Vf can be prepared only
by cascade condensation of 2-naphthylamine, aldehydes
IIe and IIf, and dimedone, because in reaction of 2-naph-
thylamine with N-methyl-5-arylpyrrole-2-carbaldehydes
IIe and IIf we failed to isolate the pure azomethines from
the reaction mixture.
Azomethine IIIа–IIId, according to the suggested re-
action scheme, adds a dimedone molecule to form unsta-
ble intermediate A, which then decomposes into arylidene
diketone B and 2-naphthylamine. In 2-naphthylamine,
the electron density is the highest at the α-carbon atom
relative to the amino group, and it undergoes addition via
this atom to the double bond of arylidene diketone B to
form compound C whose heterocyclization with water
elimination yields the ﬁ nal products, 9,9-dimethyl-12-
[(5-aryl-2-furyl) (or 5-aryl-2-thienyl, or 5-aryl-1-methyl-
11-ones Va–Vf. The possibility of the occurrence of such
transformations in the course of ternary condensation of
aromatic aldehydes, 1,3-diketones, and 2-naphthylamine
was reported in [2, 3].
The physicochemical constants of the synthesized di-
hydrobenzoacridinones Va–Vf are given in Table 1.
H NMR spectra of dihydrobenzoacridinones
Va–Vf in all the cases are superpositions of the spectra
of different fragments and consist of three fragments:
(1) seven-spin system of aromatic protons belonging to