Aromatic glyoxalimines in criss-cross cycloaddition reactions

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Authors

VERNER Jiří POTÁČEK Milan

Year of publication 2004
Type Article in Periodical
Magazine / Source Central European Journal of Chemistry
MU Faculty or unit

Faculty of Science

Citation
Field Organic chemistry
Keywords 1;4-diazabuta-1;3-dienes; criss-cross cycloaddition; perhydroimidazo[4;5-d]imidazole-2;5- dithiones; 1;3-dipole intermediate; 5-(4-substituted phenylamino)-3-(4-substituted phenyl)2-oxoimidazolidin-4-yl acetate
Description 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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