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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
Author(s) -
Schulz Martin,
Michnacs Marion,
Görls Helmar,
Anders Ernst
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900300
Subject(s) - chemistry , halide , aqueous solution , molecule , hydroxide , octahedron , ion , medicinal chemistry , guanidine , metal , copper , metal halides , polymer chemistry , stereochemistry , inorganic chemistry , organic chemistry
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)