Bromination, Iodination and Phenylation of Thianaphthenes

Gaertner, Russell

doi:10.1021/ja01139a508

Cited by 28 publications

(6 citation statements)

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“…The reaction of phenylboronic acid with diols in the presence of MgSO4 in benzene gave phenylboronates. 4-Iodo-1,2-(methylenedioxy)benzene, 21 4-iodo-N,N-dimethylaniline, 22 2-iodopyridine, 15d 3-iodobenzothiophene, 23 and aryl triflates 24 were prepared by the literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

et al. 1998

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The carbonylative cross-coupling reaction of arylboronic acids with aryl electrophiles (ArI, ArBr, and ArOTf) to yield unsymmetrical biaryl ketones was carried out in anisole at 80 °C in the presence of a palladium catalyst and a base. The reaction selectively proceeded under an atmospheric pressure of carbon monoxide when PdCl2(PPh3)2 (3 mol %)/K2CO3 (3 equiv) were used for aryl iodides and PdCl2(dppf) (3 mol %)/K2CO3 (3 equiv)/KI (3 equiv) for the bromides or the triflates. The carbonylation of arylboronic acids with benzyl halides gave aryl benzyl ketones.

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Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

et al. 1998

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“…2-(2-Methylbenzo[ b ]thiophen-3-yl)-3-(2- l -menthoxybenzo[ b ]thiophen-3-yl)maleimide ( 1 ) and 2-(2-methylbenzo[ b ]thiophen-3-yl)-3-(2- d -menthoxybenzo[ b ]thiophen-3-yl)maleimide ( 2 ) were synthesized according to the following reaction route (Scheme ). 2-Iodobenzo[ b ]thiophene ( 3 ) was prepared by the literature method 1 …”

Section: Methodsmentioning

confidence: 99%

Asymmetric Photocyclization of Diarylethene Derivatives

1997

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Diarylethene derivatives, which have an optically active l- or d-menthyl group at the 2-position of benzo[b]thiophene ring, were synthesized. Irradiation with 450 nm light in solution led to the formation of diastereomer pairs of the closed-ring forms. The product ratio of the diastereomers was dependent on solvent polarity and temperature. In slightly polar (or polarizable) solvents, such as THF and toluene, an asymmetric photocyclization was observed. At −40 °C in toluene, a diastereomer excess as large as 86.6% was observed. The mechanism of the asymmetric photocyclization is discussed.

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“…2-Iodobenzothiophene. 23 Benzothiophene (10 g, 75 mmol) was dissolved in ether (100 mL). The solution was cooled to 0 °C, and butyllithium (1.6 M in hexane, 49 mL, 78 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

trans-2-Aryl-N,N-dipropylcyclopropylamines: Synthesis and Interactions with 5-HT_1A Receptors

et al. 1996

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Twelve N,N-dipropyl-substituted derivatives of trans-2-arylcyclopropylamine have been prepared and assayed for their ability to displace [(3)H]-8-OH-DPAT from rat brain 5-HT(1A) receptors. The new derivatives include phenyl (7a), bromo- (7b) and fluorophenyl (7c-e), 2-methoxy-5-fluorophenyl (7h), and 2-hydroxy-5-fluorophenyl (7l) as well as trifluoromethylphenyl (7f) and 2,3-dichlorophenyl (7g) analogues. In the present series of compounds, electron-withdrawing substituents in the phenyl ring appear to decrease the affinity for 5-HT(1A) receptors. In contrast, electron-rich aryl groups, such as 2- or 3-thienyl (7j and 7k, respectively), provide compounds with high affinity. The additional bulk produced by the aromatic moiety in the 2-benzothienyl derivative 7i appears to be detrimental to 5-HT(1A) receptor affinity. The racemic mixtures of the interesting 7j and 7l were resolved into the enantiomers; 7j and 7l exhibited a high enantiomeric 5-HT(1A) receptor affinity ratio (75-fold and 100-fold, respectively). The enantiomers of 7j and 7l were evaluated in vivo by use of biochemical and behavioral tests in rats. Compound (1R,2R)-7j behaved as a partial agonist whereas (1R,2S)-7l appeared as an efficacious 5-HT(1A) receptor agonist, stimulating both autoreceptors and postsynaptic receptors.

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Bromination, Iodination and Phenylation of Thianaphthenes

Cited by 28 publications

References 1 publication

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

Asymmetric Photocyclization of Diarylethene Derivatives

trans-2-Aryl-N,N-dipropylcyclopropylamines: Synthesis and Interactions with 5-HT_1A Receptors

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Bromination, Iodination and Phenylation of Thianaphthenes

Cited by 28 publications

References 1 publication

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

Asymmetric Photocyclization of Diarylethene Derivatives

trans-2-Aryl-N,N-dipropylcyclopropylamines: Synthesis and Interactions with 5-HT1A Receptors

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trans-2-Aryl-N,N-dipropylcyclopropylamines: Synthesis and Interactions with 5-HT_1A Receptors