Polycyclic ferrocenyl-4,5-dihydropyrazoles in nucleophilic reactions with β-dicarbonyl compounds
摘要:
Polycyclic ferrocenyldihydropyrazoles with a free -NH group react with ethyl acetoacetate and acetylacetone to give the corresponding enamino carbonyl compounds isolated as E-isomers. The spatial structure of (E)-4-[1-(ethoxycarbonyl)prop-2-en-2yl]-3-ferrocenyl-1,4,5-triazatricyclo[5.2.2.0(2.6)]undec-5-ene was determined using X-ray diffraction analysis. Spontaneous isomerization of (E)-(4-oxopent-2-en-2-yl)(ferrocenyl)dihydropyrazoles into the respective Z-isomers was observed. (C) 2002 Elsevier Science B.V. All rights reserved.
Asymmetrical induction in the synthesis of bicyclic pyrazolines with a ferrocenyl substituent has been studied. A relatively high diastereomeric selectivity in the 'chiral-center-by-a-chiral-center' induction of the 1,2-type has been observed. Molecular geometry of a cis-diastereomer of 1-acetyl-9-ferrocenyl-4-ferrocenylmethylene-1,2-diazabicyclo[4.3.0]non-2-ene has been established. Bicyclic 2-pyrazolines having conjugated ferrocenylmethylene fragments interact with azodicarboxylic acid N-phenylimide to form diene and monoene adducts. (C) 1999 Elsevier Science S.A. All rights reserved.