Synthesis of the Dopamine Agonist (-)-Quinpirole

Schaus, John M.; Huser, Diane L.; Titus, R. D.

doi:10.1080/00397919008051599

Cited by 20 publications

(4 citation statements)

References 5 publications

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“…Not surprisingly, enamines are smoothy reduced to amines with NaBH 4 /HOAc as shown for 35 − 37 . − This method has been applied to dienamines …”

Section: Chemistry Of Acyloxyborohydridesmentioning

confidence: 96%

The Synthetic Versatility of Acyloxyborohydrides

Gribble

2006

Org. Process Res. Dev.

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Acyloxyborohydrides are unsurpassed in their versatility as reagents in organic synthesis. In addition to their superior ability in effecting reductive amination of aldehydes and ketones, acyloxyborohydrides can reduce nitrogen heterocycles (indoles, quinolines, isoquinolines), imines, enamines, oximes, amides, nitriles, benzylic alcohols, aryl ketones, aldehydes (but not ketones), acetals, -hydroxy ketones, and other substrates. The ability to control chemoselectivity, regioselectivity, and stereoselectivity by adjusting the carboxylic acid, borohydride reagent, stoichiometry, and temperature has no parallel in the repertoire of the organic chemist.

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“…Not surprisingly, enamines are smoothy reduced to amines with NaBH 4 /HOAc as shown for 35 − 37 . − This method has been applied to dienamines …”

Section: Chemistry Of Acyloxyborohydridesmentioning

confidence: 96%

The Synthetic Versatility of Acyloxyborohydrides

Gribble

2006

Org. Process Res. Dev.

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“…In an analogous fashion, the regioselective formylation using t -BuOK/ethyl formate and subsequent condensation with hydrazine afforded the respective N -allyl intermediate 6c in 74% yield, which was then hydrogenated to provide the target compound 6d . The regioselectivity of the heteroannelation reaction was confirmed when it was observed in the EIMS spectra of the N -allyl compounds 5b and 6c that the base peak at m / z 170 was derived from a thermally promoted retro -[4+2] reaction, cleaving the tetrahydropyridine ring with generation of the N -allyl isoquinolinium cation (after elimination of an H radical and rearomatization of the corresponding parent ion, m / z 171).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Dopaminergic Properties of Benzo-Fused Analogues of Quinpirole and Quinelorane

et al. 1999

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In an analogy to the potent catechol dopamine D1 agonists dihydrexidine (1) and dinapsoline (2), benzo rings were fused onto the structures of the dopamine D2-selective agonists quinelorane (3) and quinpirole (4). Each of the phenyl ring-substituted derivatives had significant affinity for D2 receptors, albeit somewhat lower than the two parent compounds, 3 and 4. Compounds with N-propyl and N-allyl substituents (5b, 5c, 6c, and 6d) had higher affinity for the D2 dopamine receptor than did their corresponding secondary amines (5a and 6a). Slightly different effects on affinity of an n-propyl and an n-allyl group in the new analogues of 3 and 4 suggest that different binding orientations may be invoked at the receptor.

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“…Due to the potentially different pharmacological activities of the enantiomers of a chiral drug molecule, there is an interest in enantioselective synthetic methods that provide access to a single enantiomer of drug substances. Synthetic analogues of ergot alkaloids are of great interest in the pharmaceutical and agrochemical industry because they exhibit a wide spectrum of physiological activities . In particular, quinagolide 1 is a dopamine agonist that has shown significant activity at the D 2 dopamine receptor level on the surface of lactotroph cells in the anterior pituitary gland, resulting in inhibition of the prolactin secretion (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Streamlined Stereoselective Entry to (−)-Quinagolide and to 3-Substituted Octahydrobenzo[g]-Quinolines

Sardelli,

Comparini,

Favero

et al. 2024

J. Org. Chem.

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A very short stereoselective synthesis of enantiomerically pure (3S, 4aS, 10aR)-quinagolide has been developed. The key steps involved are a copper-catalyzed regioselective arylation of (S)-epichlorohydrin with 1,6-dimethoxynaphthalene and a diastereoselective trans-reduction of a cyclic enamine intermediate. The possibility to use both enantiomers of epichlorohydrin and the diastereodivergency found in the reduction process paves the way for a general preparation also in the nonracemic form of chiral trans-fused 3-substituted octahydrobenzo[g]quinolines that are privileged structures in medicinal chemistry.

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Synthesis of the Dopamine Agonist (-)-Quinpirole

Cited by 20 publications

References 5 publications

The Synthetic Versatility of Acyloxyborohydrides

The Synthetic Versatility of Acyloxyborohydrides

Synthesis and Dopaminergic Properties of Benzo-Fused Analogues of Quinpirole and Quinelorane

Streamlined Stereoselective Entry to (−)-Quinagolide and to 3-Substituted Octahydrobenzo[g]-Quinolines

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