Two directions of interaction of enamino- and azaenaminoindoles with
dienophiles
A.D. Ivina, К.I. Lugovik и N.P. Belskaya
Urals Federal University, 620002 Russia, Ekaterinburg, Mira Str. 19
E-mail: ivina.anna@mail.ru
The indole moiety is one of the most important heterocycles, which is present as structural
core in a numerous natural compounds and pharmaceuticals.[1, 2] It is known, that introduction of
substituents and functional groups into the structure of molecule, has great importance for synthesis
of novel fused heterocyclic derivatives. From this point of view, enamine and hydrazone groups are
of interest as an extremely reactive moiety.
The study of interaction of the enamines (Х=СН) or azaenamines (Х=N) 1 and
acetylenedicarboxylate esters led to formation of 3-oxothiazolo[3,2-a]indoles 2 through the as a
result of the addition/ heterocyclization mechanism.
Схема 1
Enaminoindoles 1 (Х=СН) react with N-methyl- or N-phenylmaleimides under mild
conditions to form a tetracyclic product 3 with moderate to high yields. Opposite, reaction of
azaenaminoindoles (Х=N) and maleimides didn’t realized despite the use of night temperature.
Литература
[1] N. Karali, O. Guzel, N. Ozsoy , S. Ozbey c, A. Salman. Eur. J. of Med. Chem., 2010, 45, 1068–1077
[2]. F. M. Moghaddam, B. K. Foroushani , M. Sobhani, N. Masoud, M. R. Khodabakhshi, N. S. Weng. Tetrahedron,
2013, 69, 8169-8173