1329
Amidines are known reagents in some synthetic methods
for obtaining heterocyclic compounds as well as they are
used as suitable reagents in numerous cycloaddition processes.
An example of their application is the synthesis of
pyrimidines and imidazoles shown by Vidal and coauthors.
1
Also, a new efficient and convenient approach was
proposed to the synthesis of pyrimidines by Cu-catalyzed
and 4-HO-TEMPO-mediated [3+3] annulation of commer-
cially available amidines with saturated ketones.
2
On the
other hand, diazaheterocyclic compounds are interesting
from various scientific aspects
3
and have a significant
potential as modern functional materials,
4
as well as they
could be considered as objects which have a significant
interest from the point of view of biological activity.
5
The aim of the work was to develop on the basis
of known procedures
6
a method for the synthesis of
N,N'-unsubstituted α-aminoamidines and ways for their
further modification to synthesize new promising imidazole-
and pyrimidine-containing compounds.
We proposed and optimized a convenient and affordable
pathway for the synthesis of previously undescribed
α-aminoamidines 4a–e starting from N-protected amino-
nitriles 1a–e, which can be easily obtained by described
methods (Scheme 1).
7,8
The key stage of the approach is a
procedure of hydrogenation of O-acetyl-substituted amino-
oximes 3a–e in the presence of palladium catalyst.
9,10
It
should be noted, that our attempts to perform direct
reduction of aminooximes 2a–e to aminoamidines 4a–e
were unsuccessful, though such transformations for
amidines had been described in literature earlier.
11–16
Therefore, we carried out preliminary O-acylation of
compounds 2a–e by acetic anhydride.
Chemistry of Heterocyclic Compounds 2020, 56(10), 1329–1334
Efficient synthesis of imidazole and pyrimidine derivatives
Oleksii O. Kolomoitsev
1
*, Eugene S. Gladkov
1,2
, Volodymyr M. Kotlyar
1
, Polina I. Pedan
3
,
Oleksandr V. Onipko
3
, Oleksandr V. Buravov
3
, Valentyn A. Chebanov
1,2
1
V. N. Karazin Kharkiv National University,
4 Svobody Sq., Kharkiv 61022, Ukraine; е-mail: o.o.kolomoitsev@karazin.ua
2
State Scientific Institution ''Institute for Single Crystals'', National Academy of Sciences of Ukraine,
60 Nauky Ave., Kharkiv 61072, Ukraine
3
Enamine Ltd.,
67 Chervonotkatska St., Kyiv 02660, Ukraine
Submitted March 5, 2020
Accepted after revision July 9, 2020
A convenient and affordable synthetic pathway for obtaining new α-aminoamidines starting from aminonitriles is proposed. The
α-aminoamidines obtained can be applied as substrates for further transformations and synthesis of imidazole- and pyrimidine-containing
building blocks.
Keywords: α-aminoamidine, 1-chloropropan-2-one, 3-(diethylamino)prop-2-enal, heterocycle, imidazole, pyrimidine.
Scheme 1
Published in Khimiya Geterotsiklicheskikh Soedinenii,
2020, 56(10), 1329–1334
0009-3122/20/56(10)-1329©2020 Springer Science+Business Media, LLC