Zur Umsetzung von Oxalamidinen mit Heterocumulenen der Kohlensäurereihe zu Imidazolidin‐Derivaten

• Published in: Journal für Praktische Chemie
• Main Authors: Beckert, R., Gruner, M.
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 1990
• Subjects: Carbonic acid
• Online Access: http://dx.doi.org/10.1002/prac.19903320108; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fprac.19903320108; https://onlinelibrary.wiley.com/doi/pdf/10.1002/prac.19903320108

On the Reaction of Oxalic Amidines with Carbonic Acid Derived Heterocumulenes to Imidazolidine‐Derivatives A useful synthetic route to nonsymmetric derivatives of imidazolidine (derivatives of parabanic acid) is demonstrated by the reaction of tetraarylated oxalic amidines 1 with different alkyl‐ and aryl substituted isothiocyanates 4 , isoselenocyanates 31 , and carbodiimides 30 . Acylisothiocyanates 9 react differently leading to a mixture of three cycloacylation products 12 , 13 and 14 . Silylated heterocumulenes such as 25 and 26 react with 1 to give 28 and 29 transsilylation. Based on the 13 C‐n.m.r. spectroscopic investigation of the reaction between 1a and methyl isothiocyanate and phenyl isothiocyanate respectively a mechanism is proposed.