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2005
Cyclopropane derivatives
Q 0021
Reactions of Heteroaryl Substituted Propenones. — Thienyl- and furylpropenones
react with sulfur ylide (II) yielding heteroaryl substituted cyclopropyl ketones (III)
36- 056 (I)
which are transformed into dihydrobenzofuranone and -thiophenone (IV), or γ-hydroxy
ketones (V) and (VI) by reaction of cyclopropyl ketones with Lewis acids. Reaction of
(I) with activated methylene compounds (VII) and (XI) affords the corresponding addition products which can be cyclized to heteroaryl substituted dihydropyranes, e.g.
(IX), cyclohexanols, e.g. (XII) and piperidones, e.g. (XIV). Compounds (XII) and
(XIV) are examples of unusual cyclization products. In addition, cycloadditions with
thiophene derivatives enable the synthesis of substituted benzothiophene derivatives,
but with poor yields. — (GREINER-BECHERT, L.; SPRANG, T.; OTTO*, H.-H.;
Monatsh. Chem. 136 (2005) 4, 635-653; Inst. Pharm./Med. Chem.,
Ernst-Moritz-Arndt-Univ., D-17487 Greifswald, Germany; Eng.) —
H. Hoennerscheid
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