Anodic oxidation of 1,2,3,4-tetrahydronaphthalene and isochroman analogs of 1-benzyl and 1-phenethyl isoquinoline alkaloids. Products and mechanism of the intramolecular cyclization

Palmquist, Ulf; Nilsson, Anders; Pettersson, Tore; Ronlán, Alvin; Parker, Vernon D.

doi:10.1021/jo01316a008

Cited by 15 publications

(3 citation statements)

References 9 publications

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“…25,26 This analogy has been exploited and several studies report on the use of isochromans as starting materials or intermediates for the synthesis of iso-quinoline derivatives and vice versa , as well as for the preparation of other nitrogen-containing heterocycles. 26 Numerous methods have been developed to synthesize isochromanes by intramolecular C-O 7, 27-29 or C-C bond 30,31 cyclization.…”

Section: Resultsmentioning

confidence: 99%

Application of ortho-acylated phenylacetic acid esters to the synthesis of 1-substituted isochromanes

Ivanov¹,

Nikolova²,

Kochovska³

et al. 2007

Arkivoc

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Section: Resultsmentioning

confidence: 99%

Application of ortho-acylated phenylacetic acid esters to the synthesis of 1-substituted isochromanes

Ivanov¹,

Nikolova²,

Kochovska³

et al. 2007

Arkivoc

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“…Photolyses were performed with a Hanovia photochemical reactor using a 125-W lamp with a quartz immersion well. (5).--This compound was prepared using the conditions described previou~ly.~ Its authenticity was confirmed by comparison, mixed melting point, i.r. spectroscopy and t. Electrolysis of Laudanosine.-Laudanosine was electrolysed at an anode potential of ca.…”

Section: N N(ne) Acmentioning

confidence: 99%

Electrochemical oxidation of aromatic ethers. Part 8. Evidence of homogeneous electron transfer during the ‘low potential’ oxidation of laudanosine

Hutchins¹,

Sainsbury²,

Scopes³

1983

J. Chem. Soc., Perkin Trans. 1

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Photoiysis of N-amino-and N-nitroso-derivatives of 1,2,3,4-tetrahydropapaverine fails to produce arylaryl coupled products analogous to 0-methylflavinantine. Instead both the 1and 2-substituents of the heterocyclic ring are cleaved to give 6,7-dimethoxy-3,4-dihydroisoquinolines and veratraldehyde, the latter being an oxidation product of the 3,4-dimethoxybentyl radical and/or cation. From this evidence, and the results of an electrolysis experiment carried out at high dilution, it is considered that the anodic cyclisation of laudanosine to 0-methylflavinantine proceeds through homogeneous electron transfer rather than via homoconjugative activation within the intermediate radical cation as proposed by other workers.

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“…The key intermediate 9 was prepared by condensation of the known keto acid 10 , with ( S )-phenylglycinol under reflux with toluene as the solvent (Scheme ). Azeotropic removal of water left the bicyclic lactam 9 as a single diastereomer in 90% yield.…”

mentioning

confidence: 99%

A Novel Asymmetric Route to the 1,3-Disubstituted Tetrahydroisoquinoline, (−)-Argemonine

Munchhof

Meyers

1996

J. Org. Chem.

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Anodic oxidation of 1,2,3,4-tetrahydronaphthalene and isochroman analogs of 1-benzyl and 1-phenethyl isoquinoline alkaloids. Products and mechanism of the intramolecular cyclization

Cited by 15 publications

References 9 publications

Application of ortho-acylated phenylacetic acid esters to the synthesis of 1-substituted isochromanes

Application of ortho-acylated phenylacetic acid esters to the synthesis of 1-substituted isochromanes

Electrochemical oxidation of aromatic ethers. Part 8. Evidence of homogeneous electron transfer during the ‘low potential’ oxidation of laudanosine

A Novel Asymmetric Route to the 1,3-Disubstituted Tetrahydroisoquinoline, (−)-Argemonine

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