Nucleophilic aromatic substitution reactions with the fluoride ion: formation of 5-fluoroindanones and indandiones related to atipamezole
The 5-nitro and 5-(trimethylammonium trifluoromethanesulfonyl)indanones 2a,b and the related 1,3-indandiones 3a,b have been synthesized, and the efficiency of the nucleophilic aromatic substitution reaction with fluoride ion on these substrates evaluated.The indandiones underwent aromatic substitution to afford fluoroaromatic adducts whereas the indanone substrates provided little or no fluoro-substitution product.The fluoroindandione was subsequently reduced to the corresponding fluoroindane hydrocarbon.The synthetic sequence of nucleophilic fluorination followedby carbonyl reduction provides a rationale for the potential preparation of the radiofluorinated α2-adrenoreceptor ligand 5-fluoroatipamezole.
Enas, J. D.,Garcia, J. G.,Mathis, C. A.,Gerdes, J. M.
Enantioselective Synthesis of Indanes with a Quaternary Stereocenter via Diastereoselective C(sp3)-H Functionalization
A practical synthesis of enantioenriched indane derivatives with quaternary stereocenters was developed via sequential enantioselective reduction and C-H functionalization. Good to excellent enantioselectivity could be achieved by either the CuH-catalyzed asymmetric reduction or the Corey-Bakshi-Shibata (CBS) reduction of indanone derivatives. The subsequent diastereospecific and regioselective rhodium-catalyzed silylation of the methyl C-H bond led to indane derivatives with quaternary centers. This strategy was further applied in syntheses of (nor)illudalane and botryane sesquiterpenoids.
Chen, Jun,Shi, Zhan,Lu, Ping
supporting information
p. 7359 - 7363
(2021/10/01)
KCNQ 2-5 CHANNEL ACTIVATOR
An object of the present invention is to provide a novel compound having a strong opening action with respect to KCNQ2-5 channels. A compound represented by the general formula (I) (wherein the definition of each group is as described in the specification) is provided. The compound represented by the general formula (I) has a strong opening action with respect to KCNQ2-5 channels, and therefore is useful as a prophylactic and/or therapeutic agent for a KCNQ2-5 channel-related disease (for example, dysuria, overactive bladder, or the like).
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Paragraph 0257
(2019/03/06)
Synthesis of α-indanones via intramolecular direct arylation with cyclopropanol-derived homoenolates
A palladium-catalysed, tandem cyclopropanol rearrangement and direct arylation approach for the synthesis of 1-indanones is reported. The reaction is generally high yielding, uses oxygen as the terminal oxidant and tolerates a range of functional groups on the aryl ring.
Rosa, David,Orellana, Arturo
supporting information; experimental part
p. 1922 - 1924
(2012/03/11)
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