1,3-Acylumlagerungen bei der Cyclisierung von Thioharnstoffen mit Imidoylchloriden der Oxals�ure - Ein Zugang zu interessanten Thiocarbonylsystemen
摘要:
By cycloacylation of various substituted thioureas with bis-imidochlorides of oxalic acid the new thiazolidines 3, 4 and isomeric imidazolidines 5, 6 are obtained. Especially when triethylamine is used as a base the main products are the deeply coloured 4-arylimino-5-thioxo-imidazolidines which can be regarded as s-cis-configurated 1,4-dihetero-1,3-dienes. Some thiazolidines can be rearranged by means of anhydrous organic acids to parabanic acid derivatives; whereas the 5-thioxo-imidazolidines result from an intramolecular 1,3-acyl rearrangement during the reaction.
1,3-Acylumlagerungen bei der Cyclisierung von Thioharnstoffen mit Imidoylchloriden der Oxals�ure - Ein Zugang zu interessanten Thiocarbonylsystemen
作者:R. Beckert、M. Gruner
DOI:10.1002/prac.19923340711
日期:——
By cycloacylation of various substituted thioureas with bis-imidochlorides of oxalic acid the new thiazolidines 3, 4 and isomeric imidazolidines 5, 6 are obtained. Especially when triethylamine is used as a base the main products are the deeply coloured 4-arylimino-5-thioxo-imidazolidines which can be regarded as s-cis-configurated 1,4-dihetero-1,3-dienes. Some thiazolidines can be rearranged by means of anhydrous organic acids to parabanic acid derivatives; whereas the 5-thioxo-imidazolidines result from an intramolecular 1,3-acyl rearrangement during the reaction.