Kalman Harsanyi

Crystal and molecular structure of 5-diacetylamino-3,4-diphenylisoxazole

The structure of (IV) the acetylation product of 5-amino-3,4-diphenylisoxazole has been investigated by spectroscopic methods and determined from three-dimensional X-ray diffraction data. Crystals are orthorhombic, space group P212121 with Z= 4 in a unit cell of dimensions: a= 9·216(4), b= 9·324(5), and c= 19·043(8)A. The crystal structure has been solved by direct methods and refined by block-diagonal least-squares to R 0·063 (1282 independent reflections). The bond lengths of the isoxazole and of the phenyl rings are as expected. The two bonds linking the phenyl rings to the central isoxazole ring, however, are significantly shorter (1·449 and 1·450 A) than expected for the C(sp2)–C(sp2) bond (1·482 A). The planes of the phenyl rings and of the two acetyl groups are twisted differently about the bonds linking them to the isoxazole ring.

An unexpected ring transformation of (Z)-3-benzyl-2-(nitromethylene)thiazolidine

An unexpected ring enlargement, accompanied by oxidative–reductive transformation of the nitromethylene group, was brought about in almost quantitative yield by the reaction of (Z)-3-benzyl-2-(nitromethylene)thiazolidine (1a) and sodium hydroxide. The suggested mechanism is based on MS measurements involving isotope-labelled compounds.

DIPHENYLPROPYLAMINDERIVATE 4. MITT. SYNTH. DES N-METHYL-3,3-BIS-(4-AMINOPHENYL)-PROPYLAMINS

Das N-Methyl-3,3-bis-(4-aminophenyl)-propylamin (V) wird hergestellt, indem 3,3-Bis-(4-nitrophenyl)-propylamin (Ib) mit Benzaldehyd in die Schiffsche Base (IIb) ubergefuhrt (96%), daraus mit Dimethylsulfat und nach alkalischer Hydrolyse das monomethylierte Produkt (IIIb) erhalten (96%), (IIIb) sodann acetyliert (5 3,5%), reduziert und verseift wird (40%).