Arylhydrazones of 2,3,5,6,7,8-hexahydroacridin-4(1H)-ones and 7-amino-6-(arylhydrazono)-7-oxoheptanoic acids were cyclized by Fischer reaction, providing previously unknown polysubstituted indole derivatives. The starting hydrazones were synthesized under Japp–Klingemann reaction conditions by using 1,2,3,4,5,6,7,8-octahydroacridine-4-carboxamide and 2-oxocyclohexanecarboxamide as starting materials. It was established from the spectral data that the obtained 7-amino-6-(arylhydrazono)-7-oxoheptanoic acids existed as mixtures of (Z)- and (E)-isomers, but were converted to an individual (Z)- or (E)-isomer in DMSO solution.
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The authors would like to express their gratitude to Candidate of Chemical Sciences N. E. Borisova for performing NMR experiments. NMR spectra were acquired at the Laboratory of Magnetic Tomography and Spectroscopy, Department of Chemistry, Moscow State University.
This work received financial support from the Ministry of Education and Science of Ukraine within the framework of the State budget item No. 0115U003159 “New synthetic methods for the design of nitrogen- and sulfur-containing biologically active compounds”.
Zaliznaya, E. V.; Farat, O. K.; Gorobets, N. Yu.; Markov, V. I.; Zubatyuk, R. I.; Mazepa, A. V.; Vashchenko, E. V. Chem. Heterocycl. Compd.2015, 51, 327. [Khim. Geterotsikl. Soedin.2015, 51, 327.]Google Scholar