Ring-expansion of an Aziridinone to a Hexahydrotriazine Through the Agency of a Novel Rearrangement

Reaction of 1,3-di-t,'rt-bu~.laziridinonc (la) and similar aziridinones with thiosemicarbazide affords, as one of the products, a compound devoid of sulfur, vie., a substituted N- aminoimidazolidinone (3a) by selective cleavage of the acyl-nitrogcn bond. Compound 3a undergoes a novel, acid-catalyzed rearrangement to a 3-imino-hexahydro-1,2,4-tri~in-6-one (7a), which can also be obtained ~' treatment of la with hydrazinc followed by BrCN. involving again selective cleavage of the acyl-nitrogen bond

Regioselectivity in nucleophilic ring-opening of aziridinones

The proportions of products derived from competing modes of ring-opening of 1,3-di-tert-butylaziridinone and similar aziridinones by a variety of nitrogen, oxygen, sulfur and halogen nucleophiles do not agree with simple guidelines postulated in the literature for these types of aziridinones

Crystal structure of 1,5-di-tert-butyl-2-iminoimidazolidin-4-one, C11H21N3O

Source of material : The title compound was prepared by treatment of 1,3-di-tórí-butylaziridinone with cyanamide, followed by trituration with ether as described in ref. 1

Crystal structure of 1,5-di-tert-butyl-2-(methylamino)-2-imidazolin-4-one monohydrate, C12H24N3O1.5

Source of nnaterial: The title compound was prepared by treatment of 1,3-di-fert-butylaziridinone with methylthiourea, followed by chromatography on silica gel, and crystallization from toluenehexane as reported in ref. 1

Synthesis and X-ray Analysis of (RS)-N-tert-butyl-2-anilino- 3,3-dimethylbutanamide

The crystal and molecular structure of (RS)-N-Tert-butyl-2-anilino-3,3-dirnethylbutanamide, a derivative of an amino acid that was obtained by highly selective cleavage of 1,3-di-tert-butylaziridinone by aniline, is described. The racemic mixture of the amide crystallizes in the space grot)p P 2in with four molecules per unit cell. Crystal Data: a - 10.483(2) A, h - 6.206(I) A, c = 24.767(5) A, [3 - 90.39(3), V = 1611.5(6) A ~, R(F)[I > 2r = 0.0679, wR(F 2) [1 > 2or(l)] = 0. 1148

Preparation of Substituted Imidazolidinones and Hydantoins by Ring-Expansion of Aziridinones

Reaction of 1,3-di-tert-butylaziridinone and other di-tert-alkylaziridinones with cyanamides produces an imidazolidinone (3 or 6) bearing the tert-alkyl substituents at positions 1 and 5 only, by selective cleavage of the acyl-nitrogen bond. Treatment of the product from the unsubstituted cyanamide (3) with HNO 2 furnishes the corresponding hydantoin (5), whereas treatment with alkyl halides and base affords another imidazolidinone (7