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4-Silacyclohexan-1-ones 1a-1c, 4-silacyclohexan-1-one oximes 2a-2c, 1,4-azasilepan-7-ones 3a-3c, 1,4-azasilepanes 4a-4c, and 2-bromo-4-silacyclohexan-1-ones 5a and 5b were prepared in multistep syntheses, starting from trimethoxypropylsilane. All of these compounds represent C-functional (R2C═O, R2C═N-OH, R-NH(C═O)-R, R2NH, or R3C-Br) silicon-containing heterocycles that contain Si-MOP, Si-DMOP, or Si-TMOP moieties (MOP = 4-methoxyphenyl; DMOP = 2,6-dimethoxyphenyl; TMOP = 2,4,6-trimethoxyphenyl), which can be cleaved under mild conditions by protodesilylation. As a proof of principle, compounds 3a-3c were transformed quantitatively and selectively into the chlorosilane 6 (treatment with hydrogen chloride in dichloromethane). Thus, the C- and Si-functional compounds 1a-1c, 2a-2c, 3a-3c, 4a-4c, 5a, and 5b represent versatile building blocks for synthesis.

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N‐hydroxyamidines (amidoximes) may be used in prodrug technology in improving oral bioavailability of drugs containing amidino functional groups. In the body, amidoximes are reduced quickly to amidines by enzymes that are present in several organs. Ximelagatran is a benzamidoxime and ethyl ester prodrug of melagatran, which is a thrombin inhibitor. Our aim was to develop a fast and efficient labeling route for the synthesis of [11C]ximelagatran ([11C]3) with a label in a metabolically stable position. [11C]3 was synthesized via a two‐step synthesis sequence, starting from palladium catalyzed [11C]cyanation of its corresponding bromide precursor (2‐[2‐(4‐bromo‐benzylcarbamoyl)‐azetidin‐1‐yl]‐1‐cyclohexyl‐2‐oxo‐ethyl amino‐acetic acid ethyl ester) (1), followed by a reaction with hydroxylamine. [11C]3 was synthesized with 27±17% total overall decay corrected yield (specific radioactivity of 2360±165 Ci/mmol at EOS), with a total synthesis time of 45 min. A fast and efficient labeling route for the synthesis of [11C]3 was developed. Copyright © 2008 John Wiley & Sons, Ltd.