ABSTRACT
Michael-type addition of aziridinecarboxylates to 1,2-diaza-1,3-butadienes under solvent-free conditions (SFC) resulted in the formation of alpha-aziridinohydrazone adducts. In toluene under reflux, alpha-aziridinohydrazones gave imidazoles in moderate to good yields. Such a reactivity pattern is explained by 1,5-electrocyclization of azavinyl azomethine ylide generated through thermal ring opening of alpha-aziridinohydrazones.
ABSTRACT
A series of cis- and trans-isomeric aziridines has been studied under electron impact (EI) and electrospray ionization (ESI) conditions. The fragmentation patterns of the examined compounds have been elucidated by means of sequential product ion fragmentation experiments (MS(n)) performed using an ion trap mass spectrometer. Particular attention has been paid to isomer characterization in these precursors of azetidinones, that in turn are precursors of new beta-lactam antibiotics.
Subject(s)
Aziridines/analysis , Aziridines/chemistry , Models, Molecular , Spectrometry, Mass, Electrospray Ionization/methods , Mass Spectrometry/methods , Molecular Conformation , Molecular Structure , Molecular Weight , StereoisomerismABSTRACT
A new chiral derivatizing agent for ee determination of 1,2-diols via (1)H NMR is described. (S)-(+)-N-acetylphenylglycineboronic acid (1) is synthesized in enantiomerically pure form; its reaction with chiral diols quantitatively yields cyclic boronic esters 5a-g. The latter show a remarkably high diastereodifferentiation of proton NMR signals useful for de determination. [reaction: see text]
ABSTRACT
Levodropropizine, an antitussive drug, was prepared in high enantiomeric excess in three steps, starting from dichloroacetone (2). Monosubstitution of 2 with sodium benzoate and subsequent baker's yeast reduction stereoselectively afforded the corresponding chlorohydrin in 73% ee, which was converted to levodropropizine and enantiomerically enriched up to 95% ee by fractional crystallisation.
