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Paper | Regular issue | Vol 57, No. 10, 2002, pp.1799-1806
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9521
N-Arylation by Aryl Isocyanates as a General Reaction: Useful Route to Disubstituted S,N-Diarylisothioureas

Alan R. Katritzky,* Xiaohong Cai, Vladimir Y. Vvedensky, Boris V. Rogovoy, Behrouz Forood, and Normand Hebert

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


N-Arylation of guanidines, isoureas and isothioureas by aryl isocyanates is demonstrated to have generality. Novel N′-arylations of S-arylisothioureas (16) with aryl isocyanates provide a new general route to biologically active S,N′-diarylisothioureas (13). Formation of (13) is explained as [2+2] cycloaddition of isoureas (16) to isocyanates followed by elimination of HNCO.