STUDY OF THE REACTIVITY OF 2-BENZYLIDENE[3]FERROCENO-PHANE-1,3-DIONE WITH ETHYL ACETOACETATE AND SOME OTHER C-NUCLEOPHILES

Michael addition of C-nucleophiles to 2-benzylidene[3]ferrocenophane-1 ,3-dione has been studied. In some cases, (ethyl acetoacetate, acetyla cetone and malononitrile as the C-nucleophiles) the addition was follo wed by intramolecular cyclization leading to pyran derivatives. Additi on of malononitrile gave the pyran derivative as the sole product. The Michael adducts of ethyl acetoacetate and acetylacetone can be conver ted 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. Th e H-1 NMR spectra of the products are discussed.