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Synthesis of Unusually Substituted Ureas Starting from Bis(1,3,4-thiadiazolo)-1,3,5-triazinium Halides via Oxo-imidothioate Zwitterions

✍ Scribed by Martin Schulz; Marion Michnacs; Helmar Görls; Ernst Anders

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
189 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Bis(1,3,4‐thiadiazolo)‐1,3,5‐triazinium halides 1 can be converted into various products such as guanidines or bis(azolyl)alkanes. However, they also react with hydroxide ions in aqueous solution to form novel heterocyclic‐substituted ureas 2a–i. The yields were increased from moderate to good or excellent in the presence of excess guanidine 3. The assumption that hydrogen‐bonded intermediate encounter complexes EC are formed gives a reasonable explanation for the observed reaction path. The molecular structures of some of the crystalline products 2 were determined by X‐ray analysis. Furthermore, with copper(II) a dinuclear complex 8 is formed with the two metal ions in a distorted octahedral environment; a water molecule acts as a bridging ligand between the Cu^II^ ions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Novel 5/6/5 heterocycles, 1,3,4-thiadiazolo[3,2-a]-1,3,4-latter show that both sp 2 -C atoms C(10) and C(12) of 7 are significantly positively charged and, therefore, exhibit thiadiazolo[3,2-d]-1,3,5-triazinium halides 7, have been synthesized by the reaction of 2-amino-1,3,4-thiadiazoles 6 electrop