217. The synthesis and resolution of (±)-corlumine

Whaley, Wilson M.; Meadow, Morton

doi:10.1039/jr9530001067

Cited by 28 publications

(9 citation statements)

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“…A similar discrepancy has been noted by Dhami and Stothers in the case of ortho-disubstituted anisoles (13) and attributed to sberic perturbation. Our observation that the less bulky lnethylenedioxy substituent gives shift parameters which are in close agreement with observed values at a substituted orrho carbon, such as C-7a of 14a, a i d C-8a of 21 For personal use only.…”

supporting

confidence: 77%

¹³C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds

Hughes¹,

Holland²,

MacLean³

1976

Can. J. Chem.

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The natural abundance 13C nuclear magnetic resonance spectra of a number of isoquinoline alkaloids and related model compounds have been recorded. In almost all cases comparison of the spectra of the alkaloids with those of the model compounds has permitted unambiguous assignment of the alkaloid carbon resonances. The ability of 13C nmr spectroscopy to distinguish between diastereomeric pairs of both protoberberine and phthalideisoquinoline alkaloids has been demonstrated.

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supporting

confidence: 77%

¹³C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds

Hughes¹,

Holland²,

MacLean³

1976

Can. J. Chem.

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“…6,7-dimethoxy-2-methyl-3.4-dihydroisoquinolinium iodide (27). 2-formyl-5,6-methylenedioxybenzoic acid (28).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of phthalideisoquinolines from 3-halophthamdes and 3,4-dihydroisoquinolinium salts

Slemon¹,

Hellwig²,

Ruder³

et al. 1981

Can. J. Chem.

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. Can. J. Chem. 59. 3055 (1981).Phthalideisoquinoline alkaloids have been synthesized by coupling appropriately substituted 3-halophthalides and 2-methyl-3,4-dihydroisoquinolinium salts in the presence of Zn(Cu) couple or metallic Zn. Both e n t i l r -o and rhr-ro isomers are formed in the reaction. The nmr spectra of the (C)-erythro-and (i)-thrro-isocordrastines have been rcinvestigated. The results, which differ from those previously reported. lead to a different conclusion regarding the conformation of the molecules. 3055 (1981) O n a synthetise des alkaloides du type phtalideisoquinoleines en faisant reagir des halo-3 phtalides convenablement substitues avec les sels de methyl-2 dihydro-3.4 isoquinolinium en presence du couple Zn(Cu) ou du Zn metallique. I1 se forme les deux isomeres ktythro et thr-60 au cours de la reaction. On a etudie de nouveau les spectres de rmn des isocordrastines ( f ) csr-ythr-o et ( f ) threo. Les resultats, qui different de ceux rapportes antlrieurement. conduisent a une conclusion differente en ce qui a trait a la conformation des molecules. CLARKE E SLEUON. LOUISE C HELLWIG JEAN-PIERRF RUDFR, ERIC W HOSKINS et DAVID B MACLEAY Can J Chem 59,[Traduit par le journal]

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“…Compounds Ia, Ib, Id, Ie [22], Ic [23], XIIIaXIIId [24], and XVII [25] were synthesized according to published procedures.…”

Section: Methodsmentioning

confidence: 99%

1,3-Dipolar Cycloaddition of Difluoro-Substituted Azomethine Ylides. Synthesis and Transformations of 2-Fluoro-4,5-dihydropyrroles

et al. 2005

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2-Fluoro-4,5-dihydropyrrole-3,4-dicarboxylic acid derivatives were obtained by reaction of difluorocarbene with N-substituted ketone imines in the presence of fumaronitrile, maleonitrile, or dimethyl maleate. The reaction involves intermediate formation of azomethine ylides and their subsequent cycloaddition at the double bond. 11H-Dibenz[b,e]azepine and 3,4-dihydroisoquinolines react with difluorocarbene in the presence of fumaronitrile to give fluoro-substituted dibenzo[c,f]pyrrolo[1,2-a]azepine and pyrrolo[2,1-a]-isoquinoline derivatives. Treatment of 2-fluoro-4,5-dihydropyrrole-3,4-dicarbonitrile with amines and alkoxides affords the corresponding 2-amino-and 2-alkoxy derivatives, while its reactions with hydrazine hydrate and benzimidamide lead to formation of substituted pyrrolo[2,3-c]pyrazole and pyrrolo[2,3-d]-pyrimidine derivatives.Pyrrole derivatives are widely used in synthetic and medical practice [1]. In the recent years, much attention was given to fluorinated pyrroles as potential biologically active substances. Several synthetic approaches to fluoropyrroles have been reported. Among these, direct fluorination of pyrrole derivatives [2, 3], transfunctionalization according to Schiemann [4], heterocyclization of fluorinated linear precursors [5], and 1,3-dipolar cycloaddition with participation of either fluorine-containing azomethine ylides [6][7][8] or fluorinated dipolarophiles [9, 10] must be noted.2-Fluoro-4,5-dihydropyrroles attract interest not only as potential biologically active substances but also as useful building blocks having a labile fluorine atom in the -position with respect to nitrogen. However, there are no convenient methods for the preparation of such compounds. Only two kinds of transformations are known to produce 2-fluoro-4,5-dihydropyrrole systems [11,12]. Photolytic ring contraction in N-substituted perfluoroazepines to give perfluoro-(3a,5a-dihydrocyclobuta[b]pyrroles) cannot be regarded as an acceptable synthetic route to 2-fluoro-4,5-dihydropyrroles, for its scope is limited to perfluorinated derivatives [11]. The reaction of N-methylpyrrolidone with carbonyl fluoride in the presence of cesium fluoride resulted in formation of only 4% of 2-fluoro-1-methyl-2,3-dihydropyrrole-3-carbonyl fluoride [12].We recently found that reactions of difluorocarbene with Schiff bases in the presence of 2-butenedioic acid derivatives could lead to 2-fluoro-4,5-dihydropyrroles in good yields [13]. The present article reports the results of our detailed study on the reactions of various ketone imines with difluorocarbene in the presence of fumaric and maleic acid derivatives as a method of synthesis of substituted 2-fluoro-4,5-dihydropyrroles and building up of a 2-fluoro-4,5-dihydropyrrole fragment as a part of a polycyclic system. Difluorocarbene was generated in situ by reduction of dibromodifluoromethane with lead in the presence of tetrabutylammonium bromide.The reactions of Schiff bases Ia-Id with difluorocarbene in the presence of fumaronitrile, maleonitrile, or dimethyl fumarate af...

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217. The synthesis and resolution of (±)-corlumine

Abstract: The Synthesis and Resolution of ( & ) -Corlumine . 1067 217. The Synthesis and Resolution of (&)-Corlurnine.

Cited by 28 publications

References 0 publications

¹³C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds

¹³C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds

Synthesis of phthalideisoquinolines from 3-halophthamdes and 3,4-dihydroisoquinolinium salts

1,3-Dipolar Cycloaddition of Difluoro-Substituted Azomethine Ylides. Synthesis and Transformations of 2-Fluoro-4,5-dihydropyrroles

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217. The synthesis and resolution of (±)-corlumine

Abstract: The Synthesis and Resolution of ( & ) -Corlumine . 1067 217. The Synthesis and Resolution of (&)-Corlurnine.

Cited by 28 publications

References 0 publications

13C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds

13C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds

Synthesis of phthalideisoquinolines from 3-halophthamdes and 3,4-dihydroisoquinolinium salts

1,3-Dipolar Cycloaddition of Difluoro-Substituted Azomethine Ylides. Synthesis and Transformations of 2-Fluoro-4,5-dihydropyrroles

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¹³C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds

¹³C magnetic resonance spectra of some isoquinoline alkaloids and related model compounds