Zur Reaktion von 2,4-Dioxo-4-ferrocenyl-butansäureethylester mit primären aromatischen Aminen / On the Reaction of Ethyl 2,4-Dioxo-4-ferrocenyl-butanoate with Primary Aromatic Amines

• Published in: Zeitschrift für Naturforschung B
• Main Authors: Prokop, Petra, Richter, Rainer, Beyer, Lothar
• Format: Article in Journal/Newspaper
• Language: English
• Published: Walter de Gruyter GmbH 1999
• Subjects: General Chemistry; Carbonic acid
• Online Access: http://dx.doi.org/10.1515/znb-1999-0705; https://www.degruyter.com/view/journals/znb/54/7/article-p849.xml; https://www.degruyter.com/document/doi/10.1515/znb-1999-0705/xml; https://www.degruyter.com/document/doi/10.1515/znb-1999-0705/pdf

Starting from ethyl 2,4-dioxo-4-ferrocenyl-butanoate (1) a series of new ferrocene derivatives has been prepared. While the reaction with o-phenylene diamine leads to two ferrocene-containing heterocyclic compounds, 4-ferrocenyl-3H-1,5-benzodiazepine-2-carbonic acid ethyl ester (3) and 3-(2-ferrocenyl-2-oxo-ethylidene)-3,4-dihydro-1H-quinoxalin-2-one · H 2 0 (4), reactions with m- and p-phenylene diamine give both the mono- and disubstituted products 5 - 8, respectively. The conversion of 4 by Lawesson’s reagent results in 2-ferrocenvl-thieno[2,3- b]quinoxaline (9). The new compounds have been characterized by their 1 H, 13 C NMR, and mass spectra. The molecular structures of 4-ferrocenyl-4-oxo-2-phenylamino-but-2-enoic acid ethyl ester 2, and of 4 and 9 have been determined by X-ray crystal structure analysis.