208465-07-0Relevant articles and documents
Flow Photo-Nazarov Reactions of 2-Furyl Vinyl Ketones: Cyclizing a Class of Traditionally Unreactive Heteroaromatic Enones
Ashley, William L.,Timpy, Evan L.,Coombs, Thomas C.
, p. 2516 - 2529 (2018/03/09)
Nazarov reactions of 2-furyl vinyl ketones and related heteroaromatic enones, to produce furan-fused cyclopentanones using a flow photochemical approach, are described. Compounds possessing this connectivity between heterocycle and ketone (2-furyl, 2-benzofuryl, 2-thiophene-yl, and 2-benzothiophene-yl) have traditionally proven difficult or impossible to cyclize with typical Br?nsted and Lewis acid mediated methods. Using mild flow photochemistry conditions and acetic acid (AcOH) or hexafluoroisopropanol (HFIP) as solvent, these compounds were found to cyclize in 45-97% yields, with typical UV exposure times of 3.4-6.8 min. In all cases, 2-furyl and 2-thiophene-yl enones cyclized, whereas 2-benzofuryl and 2-benzothiophene-yl enones exhibited divergent properties with reactivity patterns tied to the identity of the vinyl group. This report discloses the first photo-Nazarov reactions of tetrahydropyridine-substituted 2-furyl ketones, providing a direct approach to the corresponding fused heterocyclic motifs built around a central cyclopentanone. These motifs constitute the core structures of biologically active natural products, including the marine alkaloid nakadomarin A.
CHEMICAL COMPOUNDS
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Page/Page column 139, (2008/06/13)
The use of a compound of formula I, Y is a single bond, C=O, C=S or S(O)m where m is 0, 1 or 2; the ring is a 6 membered oaromatic ring or is a 5 or 6 membered heteroaromatic ring; Z and Z' are =C- or -N- provided that both are not N; R1/
Piperidine derivatives as reuptake inhibitors
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Page column 54, (2010/02/09)
The present invention provides compounds of formula (I) and a method of inhibiting the reuptake of serotonin and antagonizing the serotonin receptor which comprises administering to a subject in need of such treatment an effective amount of a compound of formula (I).