Ferrocene studies. V. Potential medicinal agents

Synthesis, ring transformations, IR-, NMR and DFT study of heterocycles with two ferrocenyl units

“…As it can be concluded from the almost identical values calculated for DE 2 and DE 3 (Scheme 4) the contribution to nitrilimine-stabilization from one ferrocenyl group is approximately equivalent to that provided by two phenyl groups. In accord with the calculated DE values facile thiazolone-forming cyclizations of 13 and 14 with chloroacetic acid have been reported [13,14]. In order to gain further support for the substituent-dependency of the studied models to undergo dehydrogenation, we reacted 14 with chloroacetic acid using the conditions of Methods D and E, respectively, and obtained thiazolone 16 in acceptable yields (Scheme 5).…”

“…(16) Red microcrystals; yield: 0.301 g, 46% (Method D); 0.386 g, 59% (Method E); mp 232-235°C (234-236°C in Ref. [14]); Anal. Calc.…”

Synthetic methods towards steroid-ferrocene conjugates

“…The first report for the derivatization of a steroid ketone appeared in 1970. 46 Hydrazones 86 and 87 were prepared in good-to-excellent yields by the reaction of ferrocenecarboxhydrazide (85) with androstanolone benzoate (83) Claisen-Schmidt condensation of steroidal ketones with ferrocenecarboxaldehyde (88) results in the formation of ferrocenylmethylidene derivatives, so the Fc moiety can be connected to different positions of the steroid skeleton by a C-C double bond. 16-Ferrocenylmethylidene estrone (89, Scheme 16) was prepared to be used as starting material to produce radiopharmaceuticals 47 or to carry out detailed structural investigations and bioactivity tests.…”

3,5-di-tert-butyl-1,4-benzoquinone ferrocenoylhydrazone and its zinc(II), palladium(II), and mercury(II) complexes: Structure and properties

“…It was of interest to extend a number of systems based on reverse hydrazones [16][17][18][19][20][21][22][23] using a spatially hindered fragment containing The IR spectrum of 3,5-di-tert-butyl-1,4-benzoquinone ferrocenenoylhydrazone III includes the bands of stretching vibrations of carbonyl groups of the hydrazone (1638 cm -1 ) and quinone fragments, the hydrazone C=N (1618 cm -1 ) and NH (3187 cm -1 ) bonds. The spectrum also contains the bands of torsional vibrations of cyclopentadiene rings at 481 and 500 cm -1 .…”