Synthesis of zwitterionic compounds: fully saturated pyrimidinylium and 1,3-diazepinylium derivatives via the novel rearrangement of 3-oxobutanoic acid thioanilide derivatives.
An unusual rearrangement following cyclization of 2-anilino-2-ethoxy-3-oxothiobutanoic acid with aliphatic 1,3- as well as 1,4-diamine leads to zwitterionic derivatives of 2-hydroxypropanoic acid. Moreover, with aromatic 1,2-diamines, fused heterocyclic systems such as pteridine, quinoxaline, and pyrido[2,3-b]pyrazine are obtained.
Zaleska
Barbara
B
Department of Organic Chemistry, Jagiellonian University, and Regional Laboratory of Physicochemical Analyses and Structural Research, ul. Ingardena 3, PL 30-060 Kraków, Poland. zaleska@chemia.uj.edu.pl
Bazanek
Tomasz
T
Socha
Robert
R
Karelus
Marcin
M
Grochowski
Jacek
J
Serda
Paweł
P