E. E. Korshin

UNUSUAL ANNELATION OF 2-METHYLIMIDAZOLINE WITH ARYLISOCYANATES

Reactions of acyclic amidines with isocyanates and isothiocyanates are widely used in the synthesis of 1,3diazetydinones, 1,3,5-triazine-2,4-diones, and their thioanaiogs. 1 Analogously, the interaction between 1,2dimethytimidazoline and MeNCS occurs by the same [2+2+2] cycloaddit ion stages. 2 In all these transformations the substituent at the meso-carbon of the amidine system is not affected. We have found a fundamentally different, unexpected direction o f annelat ion of 2methylimidazoline (1) with arylisocyanates (2), affecting the 2-methyl substituent and resulting in 6-aryl-8arylcarbamoyl1,2,3,5,6,7hexahydroimidazo[ 1,2c]pyrimidine-5,7-diones (6).

Aminoamidines. 5. Synthesis and acetylation of N,N1,N2-triaryl-substituted β-aminoamidines

Triaryl-substituted β-aminoamidines were obtained by the reaction of α,β-unsaturated N-arylimidoyl chlorides with arylamines. Acylation of the products gave the products from monosubstitution at the β-amino group. Triaryl-substituted β-aminoamidines react with phosgene and with oxalyl chloride to form 4-aryliminoperhydropyrimidin-2-ones and 5-aryliminoperhydro-1,4-diazepine-2,3-diones, respectively.

Reaction of aryl-substituted glycineamidines with oxalic acid derivatives

The reaction of N1,N2-diaryl-N-arylglycineamidines with oxalyl chloride and diethyl oxalate leads to 1,4-diaryl-5-aryliminopiperazine-2,3-diones and 1,3-diaryl-4-aryliminoimidazolidin-2-ones.