Collect. Czech. Chem. Commun. 2007, 72, 347-362

Heterocyclization of (Acridin-9-yl)thiosemicarbazides with Dimethyl Acetylenedicarboxylate

Jana Tomaščikováa, Ján Imricha,*, Ivan Danihela, Stanislav Böhmb and Pavol Kristiana

a Institute of Chemistry, Faculty of Science, P. J. Šafárik University, SK-041 67 Košice, Slovak Republic
b Department of Organic Chemistry, Institute of Chemical Technology, Prague, CZ-166 28 Prague 6, Czech Republic


Two types of (acridin-9-yl)thiosemicarbazides with the acridine moiety in the thiourea part (Acr-NHCS, 10a, 10b) and hydrazine part (Acr-NHNHCS, 12a-12c) were prepared to investigate their reactions with dimethyl acetylenedicarboxylate. Five-membered thiazolidinone derivatives 15a, 15b, 19a-19c were formed; some aspects of corresponding reaction mechanisms are discussed. 1D and 2D 1H and 13C NMR spectroscopy and DFT quantum chemical calculations were used to elucidate the structure of the compounds.

Keywords: Thiosemicarbazides; Thiazolidinones; Acridines; Acetylenedicarboxylate; Quantum chemical calculations; Reaction mechanisms.

References: 36 live references.