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Communication | Regular issue | Vol 51, No. 3, 1999, pp.475-479
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8418
2-Cyanamidothiazoles from 3-Propynylthio-1,2,4-triazoles

Dallas K. Bates,* Mingde Xia, Margarette Aho, Hans Mueller, and Ramani R. Raghavan

*Department of Chemistry, College of Sciences and Arts, Michigan Technological University, 1400 Townsend Drive, Houghton, Michigan, 49931, U.S.A.

Abstract

3-Allylthioallyl triazoles (5) rearrange to N-allyl derivatives (6) while 3-(2-propynyl) derivatives (2) provide 4,5-disubstituted 2-cyanamidothiazoles (9) in refluxing p-xylene. At lower temperatures N-allenyl derivatives (8) may be isolated and converted independently to 9. Intermediate allenes exhibit sigmatropic inversion of substituents characteristic of Claisen rearrangement.