Stereoselective synthesis of methyl 3,3-diarylpropenoates

Rudenko, A. P.; Savechenkov, Pavel Y.; Васильев, А. В.

doi:10.1007/s11178-005-0025-1

Cited by 10 publications

(10 citation statements)

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“…We recently initiated studies on protonation and subsequent transformations of acetylenic compounds in superacidic media [1][2][3][4][5][6], which opened new prospects in the application of superacids [7] in synthetic organic chemistry. Stang [8,9] and Olah [10] were the first to report on the addition of superacids (HSO 3 F and CF 3 SO 3 H) to alkyl-and dialkylacetylenes with formation of the corresponding vinyl fluorosulfonates and trifluoromethanesulfonates.…”

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confidence: 99%

Protonation of 3-Arylpropynoic Acid Derivatives in Superacids

Walspurger¹,

Васильев

Sommer³

et al. 2005

Russ J Org Chem

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According to the 1 H and 13 C NMR data, 3-arylpropynoic acids and their esters XC 6 H n -C C-CO 2 R (R = H, Me, Et) having electron-withdrawing substituents in the benzene ring (X = NO 2 , CN, COMe, CO 2 Me) exist in HSO 3 F at -80 to 0°C as XC 6 H n -C C-C + (OH)OR ions. Derivatives with other substituents (X = H, F, Me, MeO) in HSO 3 F or CF 3 SO 3 H above -40°C undergo protonation at the acetylenic carbon atom neighboring to the acid group to give unstable vinyl-type XC 6 H n -C + =CH-CO 2 R cations which are then transformed into mixtures of stereoisomeric (Z and E) fluorosulfonates or triflluoromethanesulfonates XC 6 H n -CY=CH-CO 2 R (Y = OSO 2 F, OSO 2 CF 3 ), the E isomer prevailing.

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confidence: 99%

Protonation of 3-Arylpropynoic Acid Derivatives in Superacids

Walspurger¹,

Васильев

Sommer³

et al. 2005

Russ J Org Chem

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“…Having established successful reaction conditions for the monomeric test system (Scheme ), we progressed to the preparation of the cyclisation precursors (Scheme ). Commercially available methyl and ethyl p ‐iodobenzoate ( 10 and 11 , respectively) were each reacted in a double Sonogashira coupling with acetylene gas to give alkynes 12 and 13 ,13 respectively, in acceptable yields 14. Palladium/charcoal‐catalysed reduction quantitatively resulted in alkanes 14 and 15 , respectively, which each underwent bromination with 1,3‐dibromo‐5,5‐dimethyl hydantoin (DBMH)15 and triflic acid (TfOH) in dichloromethane to provide the respective dibromides 16 and 17 in good yields (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 3,7‐Disubstituted Imipramines by Palladium‐Catalysed Amination/Cyclisation and Evaluation of Their Inhibition of Monoamine Transporters

Christensen

Schjøth-Eskesen

Jensen

et al. 2011

Chemistry A European J

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We describe a novel approach for the synthesis of a series of 3,7-difunctionalised symmetric and unsymmetrical analogues of the tricyclic antidepressant (TCA) imipramine, which uses a key palladium-catalysed amination/cyclisation of an ester-functionalised dibromide. Of the ester, methyl, hydroxymethyl and methoxymethyl disubstituted compounds prepared, 3,7-dimethyl-imipramine was found to be the most potent against the human serotonin transporter (hSERT). The inhibitory potency of 3,7-dimethyl imipramine was found to be at least as high as the parent imipramine. This novel TCA also exhibits an increased selectivity (relative to imipramine) in binding to hSERT versus the human norepinephrine transporter (hNET). Even higher selectivity could be obtained with 3,7-dihydroxymethyl imipramine, which was found to be 167-fold more selective for hSERT over hNET, representative of a 120-fold gain in selectivity relative to the parent imipramine. These results further validate our previous model for the binding of imipramine and high-affinity analogues of imipramine to the central binding site of hSERT.

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“…[71] or catalyzed by Ru [72] and Pd [73] were used for the synthesis of polysubstituted furans, but all attempts to obtain trifluoromethylfurans by these strategies have failed [74]. The oxidation of 4-aryl-1,1,1-trifluorobut-3-yn-2-ones in the system TFA-CH 2 Cl 2 -PbO 2 gives 2-aryl-4-arylcarbonyl-5-trifluoromethyl-3-trifluoroacetylfurans in 22-66% yield (Scheme 26) [75,76]. The formation of furans takes place in the case of ketones with electron-donating groups, such as methyl or methoxy groups.…”

Section: Heterocyclizationsmentioning

confidence: 99%

“…Several methods of 3-trifluoroacetylfurans synthesis are already described above (Scheme 26) [75,76]. less effective as a catalyst of this transformation [154].…”

Section: Heterocyclizationsmentioning

confidence: 99%