Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 692, Issue 25, Pages 5621-5632Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2007.09.017
Keywords
ferrocene; heterocycles; NMR spectroscopy; X-ray diffraction; S-O and S-N close contact; DFT calculations
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Cyclization reactions of the thiosemicarbazones of formyl- and acetylferrocene and their S-methyl derivatives with DMAD afforded novel ferrocenyl-hydrazono-substituted thiazolones, one-one dimethylthiazole-4,5-dicarboxylate and 1,3-thiazin-4-one, N-ferrocenylimino-pyrimidones/imidazolones, one intermediate P-adduct and via oxidative cyclization, a ferrocenyl-1,2,4-triazole. Ring isomerization of 1,3-thiazin-4-ones to a 1,3-thiazolones was detected. The structure of the new compounds was established by IR and NMR spectroscopy, including HMQC, HMBC and DEPT measurements and supported with GIAO NMR calculations and controlled also synthetically by phase-transfer methylation. For three compounds the stereostructure was also proved by X-ray diffraction. (C) 2007 Elsevier B.V. All rights reserved.
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