Collect. Czech. Chem. Commun. 1994, 59, 1203-1210

Cyclohexylideneacetyl Isothiocyanate. Precursor for the Synthesis of 1,3-Thiazaspirocycloalkanes and 1,3-Diazaspirocycloalkanes

Marcel Töröka, Milan Dzurillaa, Peter Kutschya, Ján Imricha, Ivan Danihela, Paul Rademacherb and Heinz Bandmannb

a Department of Organic Chemistry, Šafárik University, 040 01 Košice, Slovak Republic
b Institute of Organic Chemistry, University of Essen, D-45117 Essen, Germany


The N-(4-substituted phenyl)-N'-cyclohexylideneacetylthioureas IIa - IIf were readily prepared by the reaction of cyclohexylideneacetyl isothiocyanate I with 4-substituted anilines. They were cyclized to the 2-(4-substituted phenylimino)-4-oxo-1,3-thiazaspiro[5.5]undecanes IIIa - IIIe in the presence of boron trifluoride etherate and to the 1-(4-substituted phenyl)-4-oxo-2-thioxo-1,3-diazaspiro[5.5]undecanes IVa, IVc - IVf in alkaline medium.