117203-11-9Relevant articles and documents
Glyoxal as Synthone, III. - A Simple Synthesis of Aminopyrroles and of Dihydropyrrolopyrroles
Dieck, Heindirk tom,Verfuerth, Uwe,Diblitz, Klaus,Ehlers, Jens,Fendesak, Gert
, p. 129 - 132 (2007/10/02)
The alcoholysis of diazasilacyclopentenes 2, easily obtained from glyoxaldiimines 1 with alkali metal and dichlorosilanes, gives either 3-amino-substituted pyrroles 4 or, with only small amounts of alcohol, N-substituted dihydropyrrolopyrroles 5.Reduction of 1 with hydrogen in ethanol in the presence of small amounts of a Pd/C catalyst also gives 4 and 5, together with smaller quantities of a 3,4-diaminopyrrole 7.With more of the catalyst the formation of the 1,2-diaminoethanes 6 predominates.A single-crystal X-ray diffraction study was performed for the N,N'-di-tert-butyl derivative 5a, which confirms the expected centrosymmetric structure. - Keywords: Aminopyrroles / Diaminopyrroles / 1,4-Diaza-1,3-dienes / Glyoxal / Pyrrolopyrroles