52. Addition reactions of heterocyclic compounds. Part II. Phenanthridine and methyl acetylenedicarboxylate in methanol

Acheson, R. M.; Bond, Gary

doi:10.1039/jr9560000246

Cited by 6 publications

(2 citation statements)

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“…It is worth noting that reactions involving α addition to a phenanthridinium moiety have been reported with sulfur-based nucleophiles, carbanions, and alcohols …”

Section: Resultsmentioning

confidence: 99%

General One-Pot, Three-Step Methodology Leading to an Extended Class ofN-Heterocyclic Cations: Spontaneous Nucleophilic Addition, Cyclization, and Hydride Loss

et al. 2004

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A new class of phenanthridinium derivative has been isolated from the reaction of 2-bromoethyl-phenanthridinium bromide with a range of primary amines in excellent yields. The reaction pathway is unprecedented and proceeds via three cascade steps: nucleophilic attack of a primary amine on the iminium moiety of a heteroaromatic ring system and cyclization to form a five-membered ring, followed by hydride loss to yield a rearomatized dihydro-1H-imidazo[1,2-f]phenanthridinium derivative. A range of NMR phase transfer experiments were carried out to elucidate the mechanistic pathway, and the methodology has been further developed by means of a biphasic system using N-bromosuccinimide as a co-oxidizing agent. The method has also been extended to other N-heterocyclic cation derivatives such as quinolinium and quinazolinium.

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“…It is worth noting that reactions involving α addition to a phenanthridinium moiety have been reported with sulfur-based nucleophiles, carbanions, and alcohols …”

Section: Resultsmentioning

confidence: 99%

General One-Pot, Three-Step Methodology Leading to an Extended Class ofN-Heterocyclic Cations: Spontaneous Nucleophilic Addition, Cyclization, and Hydride Loss

et al. 2004

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“…The two structures, LIV and LV, previously proposed for labile and stable adducts of quinoline and dimethyl acetylenedicarboxylate by Diels and Alder, have been revised by Acheson and The existence of these structures in the condensation product depends on the acidity or basicity of the reaction media and the structure given is supported by the ultraviolet absorption curve and some chemical reactions undergone by it (1). The considerable differences in ultraviolet absorption spectrum between the phenanthridinium ion and the 9,10-dihydro-9-methoxyphenanthridine enable these species to be identified easily.…”

Section: Coohmentioning

confidence: 99%

Diels-Alder Syntheses with Heteroatomic Compounds.

Needleman¹,

Kuo²

1962

Chem. Rev.

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Synthèse Dans La Série Des Phenanthridines I. Recherches Des Conditions Éxperimentales Optimales Dans La Préparation D'Alkyl‐6 Phenanthridines Et De Leur Sel

Lion

Boukou-Poba

Charvy

1989

Bulletin des Soc Chimique

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The synthesis of 6-alkylphenanthridines and their corresponding salts has been developed. The well known "biphenyl method" has been studied. Acylation of o-aminobiphenyl is achieved by an acid or the corresponding anhydride or acyl chloride. Cyclization of the intermediate o-acylamidobiphenyl has been studied in various conditions (solvents, temperature ... ) Quaternization has also been accomplished: new 6-alkylphenanthridinium salts have been prepared in good yields.Une reaction d'acylation de 1'0-aminobiphhnyle suivie d'une cyclisation de l'o-acylaminobiphknyle conduit h la phdnanthridine quaternariaee en sel de phdnanthridinium : chaque dtape presente ses propres difficultds ; bien que de nombreux protocolea parfois contradictoires soient decrits dans la litterature10i14,16-zo. Nous ddcrivons ici nos resultats pour obtenir une d t h o d e simple. fiable reproductible quelques nouvellcs pMnanthridines substituees en position 6 par des groupes"sir-d'accis ples'Q1. ~s u l t a t s -Discussion Nous avons repris la sdquence de Walls en essayant d'amdliorer chaque dtape. A. ou avec son anhydride ou son chlorure : Acylation de 1'0-aminodiphCny1e.-Cette reaction a 6t6 rialisee avec l'acide carboxylique N HZ X = OH ; OCOR ; C1 1. Acylation par l'acide carboxy1ique.l'acide acdtique. Parmi lea mdthodes classiques de couplage peptidique , celle utilisant le dicyclohexylcarbodiimide (DCC)22~23 n'a pas donne lea resultats espdres (rendements trbs moyens, presence de sous-produits.. .). Par contre, la variante du N,N'-thionyldiimidazolez4~*5 dans le THF conduit quantitativement au produit attendu. Nos recherchea prhliminaires ont 6th mendes avec Cette mithode a 6th &tendue avec succbs h l'acide p-acdtylbenzolque et h l'acide lbvulinique se formulant dans ce dernier cas de la manibre suivante : N' H 3 W 2. Acylation par l'anhydride d'acide.ples (anhydrides acdtique sante l'amide correspondant, ndcessite des anhydrides difficiles h obtenirz'. 3. Acylation par lea chlorures d'acide.-Lea nombreux travaux effectuds au laboratoire28-30 Cette voie d'acylation ddcrite avec des modbles s i met propionique Iz6 si elle permet d'obtenir de manibre satisfaiont permis la mise au point de methodes performantes aux chlorures [ G I d 'acide : Schema general de synthese dcs chlorures d'acidc

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52. Addition reactions of heterocyclic compounds. Part II. Phenanthridine and methyl acetylenedicarboxylate in methanol

Cited by 6 publications

References 0 publications

General One-Pot, Three-Step Methodology Leading to an Extended Class ofN-Heterocyclic Cations: Spontaneous Nucleophilic Addition, Cyclization, and Hydride Loss

General One-Pot, Three-Step Methodology Leading to an Extended Class ofN-Heterocyclic Cations: Spontaneous Nucleophilic Addition, Cyclization, and Hydride Loss

Diels-Alder Syntheses with Heteroatomic Compounds.

Synthèse Dans La Série Des Phenanthridines I. Recherches Des Conditions Éxperimentales Optimales Dans La Préparation D'Alkyl‐6 Phenanthridines Et De Leur Sel

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