Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas

The preparation and characterization of some novel ferocenil derivatives

“…Ureas 5a-c were synthesized by the known procedure (Minić et al, 2015;Minić et al, 2020a). Spectral data of compounds 5a-c follow.…”

“…Our team have already designed and optimized reaction conditions for the synthesis of 3-arylamino-1-ferrocenylpropan-1-ones. On this occasion, which took place a few years ago, we managed to obtain high yields of the said compounds, and these proved to be both biological agents, as well as exquisite starting materials which can be used for further chemical modifications (Damljanović et al, 2011;Pejović et al, 2012a;Pejović et al, 2012b;Minić et al, 2015;Minić et al, 2017;Minić et al, 2018;Minić et al, 2019;Minić et al, 2020a). In this manner, we adapted the protocol to make it suitable for the synthesis of target compounds through the usage of iodoaniline as the arylamino moiety (see Scheme 1).…”

“…In this case, the focus is on an interest from a biological point of view (antibacterial, antimalarial, anti-inflammatory, antitumor etc.) (Minić et al, 2015;Minić et al, 2017;Minić et al, 2018;Minić et al, 2019;Minić et al, 2020a;Minić et al, 2020b;Pejović et al, 2015) The last steps consisted of premising six-membered cyclic ureas 5a-c bearing ferrocenyl group (see Scheme 1). A method which we opted for in this synthetic transformation is both efficient and involves mild reaction conditions.…”

“…A method which we opted for in this synthetic transformation is both efficient and involves mild reaction conditions. The method was earlier reported on by our research team (Minić et al, 2015;Minić et al, 2020a). We started the investigation by ultrasonicating the mixture of 1,3-aminoalcohol (4a-c) and phenyl isocyanate (0.12 ml, 1.1 mmol).…”

“…These results are a proof of our sustained interest in the synthesis of novel Fc-containing (Fc = ferrocene) heterocyclic compounds, which are of potential biological significance (Pejović et al, 2012b;Pejović et al, 2017;Pejović et al, 2018a;Pejović et al, 2018b), and in the design and optimizations of reactions conditions. 2-Ferrocenoyl ethyl aryl amines -Mannich bases have demonstrated great initial results in the synthesis of Fc derivatives (Minić et al, 2017;Minić et al, 2018;Minić et al, 2019), notably in the synthesis of sixmembered ureas (Minić et al, 2015;Minić et al, 2020a).…”