Collect. Czech. Chem. Commun.
1993, 58, 2128-2138
https://doi.org/10.1135/cccc19932128
Study of the Reactivity of 2-Benzylidene[3]ferrocenophane-1,3-dione with Ethyl Acetoacetate and Some Other C-Nucleophiles
Marta Sališováa, Ľubomír Šeboa, Štefan Tomaa and Eva Solčániováb
a Department of Organic Chemistry, Comenius University, 842 15 Bratislava, Slovak Republic
b Institute of Chemistry, Comenius University, 842 15 Bratislava, Slovak Republic
Abstract
Michael addition of C-nucleophiles to 2-benzylidine[3]ferrocenophane-1,3-dione has been studied. In some cases, (ethyl acetoacetate, acetylacetone and malononitrile as the C-nucleophiles) the addition was followed by intramolecular cyclization leading to pyran derivatives. Addition of malononitrile gave the pyran derivative as a sole product. The Michael adducts of ethyl acetoacetate and acetylacetone can be converted to [7]ferrocenophane-1,7-dione derivatives by refluxing in benzene with triethylamine as catalyst. they also easily react with ammonia, under SiO2 catalysis, to give Hantzsch dihydropyridine derivatives. The 1H NMR spectra of the products are discussed.
