Aromatic glyoxalimines in criss-cross cycloaddition reactions |
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Authors: | Verner Jiří Potáček Milan |
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Affiliation: | (1) Department of Organic Chemistry, Faculty of Science, Masaryk University of Brno, Kotlářská 2, 611 37 Brno, Czech Republic |
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Abstract: | Aromatic 1,4-diazabuta-1,3-dienes in glacial acetic acid with thiocyanates produce via criss-cross cycloaddition reactions the corresponding perhydroimidazo[4,5-d]imidazole-2,5-dithiones. When a mixture of thiocyanate and cyanate in a proper ratio was reacted together, nonsymmetrical 5-thioxo-perhydroimidazo[4,5-d]imidazole-2-ones were isolated. With cyanates substituted aromatic 1,4-diazabuta-1,3-dienes afforded product of acetic acid addition to primary formed 1,3-dipole intermediate 5-(4-substituted phenylamino)-3-(4-substituted phenyl)-2-oxoimidazolidin-4-yl acetate. |
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Keywords: | criss-cross cycloaddition glyoxalimines aromatic 1,4-diazabuta-1,3-dienes substituted 3,5-diphenyl-2-oxoimidazolidin-4-yl acetate 1,4-diphenyl-5-thioxoperhydroimidazo[4,5-d]imidazole-2-ones |
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