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Synthesis of N,N’-Linked Isothiazolium Salts via Intramolecular Cyclocondensation of Hydrazonium Salts*

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Synthesis of N,N’-Linked Isothiazolium Salts via Intramolecular Cyclocondensation of Hydrazonium Salts*

Valerija M. Zakharovaa, Anja Siegemund-Eilfelda, Joachim Sielerb, and B¨arbel Schulzea

aInstitut f¨ur Organische Chemie, Universit¨at Leipzig, Johannisallee 29, D-04103 Leipzig

bInstitut f¨ur Anorganische Chemie, Universit¨at Leipzig, Johannisallee 29, D-04103 Leipzig Reprint requests to Prof. Dr. B. Schulze. E-mail: bschulze@chemie.uni-leipzig.de

Z. Naturforsch. 61b, 464 – 470 (2006); received January 27, 2005

Interaction ofβ-thiocyanatovinyl aldehydes with N-amino heterocycles leads to formation ofα,β- unsaturated hydrazonium salts dependent on the functional surroundings. The latter can undergo further intramolecular cyclocondensation giving rise to N,N-linked isothiazolium salts as the final product. The isolated hydrazonium salts, not undergoing ring formation, have s-trans conformation of the azadiene system.

Key words:β-Thiocyanatovinyl Aldehydes, N-Amino Heterocycles, Hydrazonium Salts, Isothiazolium Salts

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