A Diastereoselective Synthesis of<i>trans/cis</i>Octahydronaphthoquinolizine

Kouvarakis, Antonios; Katerinopoulos, Haralambos E.

doi:10.1080/00397919508011436

Cited by 7 publications

(3 citation statements)

References 7 publications

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“…The resulting mixture was then cooled to room temperature, and ethyl acetate (20 mL) was added. The same workup procedure described in the above O-arylation process was followed to give product 6a as a colorless liquid . Yield: 37 mg (90%).…”

Section: Methodsmentioning

confidence: 99%

O-Arylation versus C-Arylation: Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls

Fang

2006

J. Org. Chem.

120

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The copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls via a six-membered ring closure was examined. With CuI (10 mol %) as the catalyst, N,N'-dimethylethylenediamine as the ligand, and Cs2CO3 as the base, the reactions of alpha-(2-bromobenzyl)-beta-keto esters in THF at refluxing temperature afforded the corresponding substituted 4H-1-benzopyrans in high yields via O-arylation. On the other hand, the reactions of delta-(2-bromophenyl)-beta-keto esters in refluxing dioxane led to the formation of 3,4-dihydronaphthalen-2(1H)-one derivatives via C-arylation.

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Section: Methodsmentioning

confidence: 99%

O-Arylation versus C-Arylation: Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls

Fang

2006

J. Org. Chem.

120

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“…The synthesis of the octahydrobenzo[ g ]quinoline derivatives 5a , c calls for a selective alkylation of the C-3 position of the β-tetralone systems. This known , synthetic process afforded the desired C-3-allylated products 12a , b in overall 83% and 80% yields from the corresponding β-tetralones (Scheme ). The carbonyl group was then protected as its ethylene glycol ketal, and the intermediates 13a , b were subjected to a hydroboration−oxidation reaction with disiamylborane and hydrogen peroxide−sodium hydroxide, to furnish primary alcohols 14a , b , respectively.…”

Section: Chemistrymentioning

confidence: 99%

N-(Iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines: Synthesis and Adrenergic and Dopaminergic Activity Studies

1998

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A series of N-(iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines was synthesized and assayed in vitro for their dopaminergic and alpha-adrenergic activity. Structure-activity relationship (SAR) analysis revealed that the tested benzoquinolines exhibited activity at the D1 rather than the D2 receptor sites in contrast to the D2 receptor subfamily activity reported for their aminotetralin congeners. N-Iodopropenyl substitution was apparently a decisive factor for D1 activity independent of ring substitution pattern. Considering the structural factors influencing alpha-adrenergic activity, in a general trend, N-iodopropenyl analogues were alpha1-active, with the ring-hydroxylated congeners exhibiting the highest affinity. Affinity to the alpha2 receptor was even higher with no detectable trend of SAR. However, a combination of the linear arrangement of the [g]-ring system, combined with the ring hydroxyl and the N-iodopropenyl substitution in compound 5c, resulted in a significant enhancement of alpha2 activity in this series as demonstrated by an IC50 value of 0.5 nM. A new synthetic approach to the [g]benzoquinoline system is also described.

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“…The diester was then treated with potassium tert-butoxide in Et 2 O, and the precipitated potassium salt was filtered, dried and then decarboxylated using a DMSO/H 2 O/LiCl reagent system. 30,31 The H 2 O was added in the form of concentrated HCl to neutralize the potassium salt from the previous reaction. The 2-tetralone was purified as its bisulfite adduct, which upon treatment with sodium carbonate liberated to the ketone.…”

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confidence: 99%

A Practical and Cost-Effective Synthesis of 6,7-Dimethoxy-2-tetralone

Qandil¹

1999

Synthesis

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The cyclic ketone, 6,7-dimethoxy-2-tetralone, a versatile starting material for many dopaminergic compounds, can be prepared practically, cost-effectively and in good overall yield. The synthesis starts from readily available 3,4-dimethoxyphenylacetic acid. Ring iodination gave the 2-iodo-4,5-dimethoxy acid, which was converted to its methyl ester. Palladium (II)-catalyzed Heck cross coupling afforded the expected unsaturated diester, which was then catalytically hydrogenated. Dieckmann condensation, followed by careful decarboxylation led to the desired 2-tetralone. Reagents used in subsequent reactions are inexpensive and readily available. This method appears practical for large-scale synthesis of the target tetralone, compared with other procedures reported in the literature.

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A Diastereoselective Synthesis oftrans/cisOctahydronaphthoquinolizine

Cited by 7 publications

References 7 publications

O-Arylation versus C-Arylation: Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls

O-Arylation versus C-Arylation: Copper-Catalyzed Intramolecular Coupling of Aryl Bromides with 1,3-Dicarbonyls

N-(Iodopropenyl)-octahydrobenzo[f]- and -[g]quinolines: Synthesis and Adrenergic and Dopaminergic Activity Studies

A Practical and Cost-Effective Synthesis of 6,7-Dimethoxy-2-tetralone

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