New Chemistry from the Reaction of N,N'-Disubstituted Ethylenediamines with Glyoxal: Synthesis of 2-Imidazolidinecarboxaldehydes and 1,4,6,9-Tetraalkyl-1,4,6,9-tetraaza-5,10-dioxaperhydroanthracenes

Article abstract of DOI:10.1021/jo00213a033

The reaction of N,N'-di-tert-butylethylenediamine with glyoxal in water gives initially trans-2,3-dihydroxy-1,4-di-tert-butylpiperazine, 6f, which rearranges thermally to 1,3-di-tert-butyl-2-imidazolidinecarboxaldehyde, 8f, and then to 1,4-di-tert-butyl-2