Studies on S RN1 reactions. Part 6: synthesis of 3-methyl derivatives of the alkaloids thalactamine, doryanine, and 6,7-dimethoxy-N-methyl-1(2H)-isoquinolone

Beugelmans, R.; Ginsburg, H.; Bois‐Choussy, Michèle

doi:10.1039/p19820001149

Cited by 21 publications

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“…The S RN 1 reaction of o -HO 2 CC 6 H 4 Br and derivatives with the - CH 2 COMe ion affords 78% of substitution product, which by treatment with acid gives the corresponding isocoumarin 120 (90%) (Scheme ) 45 …”

Section: Enolate Ions From Ketonesmentioning

confidence: 99%

“…Isocarbostyrils 140 are accessible by the reaction of o -bromo- or o -iodobenzamides with carbanions (Table ). The yields in the cyclization are better when the benzamides are not N-methylated (eq 134) …”

Section: F Ring Closure Reactions1 Srn1 Substitution Followed By a Ri...mentioning

confidence: 99%

“…454 The S RN 1 reaction of o-HO 2 CC 6 H 4 Br and derivatives with the -CH 2 COMe ion affords 78% of substitution product, which by treatment with acid gives the corresponding isocoumarin 120 (90%) (Scheme 45). 455 Treatment of the substitution compound obtained in the reaction of (o-iodophenyl)acetic acid derivatives with enolate ions from ketones ( -CH 2 COR, R ) Me, i-Pr, or t-Bu) upon ammonium acetate leads to the respective benzazepines 121 (Scheme 46) (50, 60, and 56% respectively). 440 Substrates with Two Leaving Groups.…”

Section: Enolate Ions From Ketonesmentioning

confidence: 99%

“…The yields in the cyclization are better when the benzamides are not N-methylated (eq 134). 455 The S RN 1 mechanism can be a route to isoquinoline rings and derivatives by reaction of o-iodobenzylamines with ketone enolate ions under irradiation (Table 56).…”

Section: S Rn 1 Substitution Followed By a Ring Closure Reaction With...mentioning

confidence: 99%

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Nucleophilic Substitution Reactions by Electron Transfer

2002

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Section: Enolate Ions From Ketonesmentioning

confidence: 99%

Section: F Ring Closure Reactions1 Srn1 Substitution Followed By a Ri...mentioning

confidence: 99%

Section: Enolate Ions From Ketonesmentioning

confidence: 99%

Section: S Rn 1 Substitution Followed By a Ring Closure Reaction With...mentioning

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Nucleophilic Substitution Reactions by Electron Transfer

2002

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Aromatic Substitution by the S_RN1 Reaction

1999

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The S RN 1 (Unimolecular Radical Nucleophilic Substitution) is a process through which nucleophilic substitution is achieved on aromatic and aliphatic compounds that do not react or react slowly through polar nucleophilic mechanisms. This transformation takes place through electron transfer steps with radicals and radical anions as intermediates. The S RN 1 mechanism was proposed for the first time in 1966 for the substitution of alkyl halides with electron‐withdrawing groups and in 1970 for the substitution of unactivated aryl halides. Since then, the scope of the process has increased considerably, and it constitutes an important synthetic method for achieving the substitution of unactivated aromatic and heteroaromatic substrates, vinyl halides, perfluoroalkyl iodides, and activated and non‐activated alkyl compounds. Nucleophiles that can be used include anions derived from carbon or heteroatoms, which react to form a new carbon‐carbon or carbon‐heteroatom bond. Several reviews have been published in relation to activated and non‐activated aliphatic S RN 1 reactions, to aromatic photoinitiated reactions, to S RN 1 reactions at aromatic centers, to reactions performed with electrochemical techniques, and to the synthetic applications of the process. This chapter attempts to cover aromatic S RN 1 reactions including all the relevant literature up to the end of 1996.

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