Electroorganic chemistry. 62. Reaction of iminium ion with nucleophile: a versatile synthesis of tetrahydroquinolines and julolidines

Shono, Tatsuya; Matsumura, Yoshihiro; Inoue, Kenji; Ohmizu, Hiroshi; Kashimura, Shigenori

doi:10.1021/ja00385a033

Cited by 96 publications

(15 citation statements)

References 1 publication

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“…In general, the reaction takes place through in situ Lewis acid‐catalyzed iminium ion formation, followed by cyclization with nucleophilic alkenes. As example, Shono et al (1982) synthesized the 1,7‐disubstituted 56 (45 % yield; Scheme ) and the 1‐substituted julolidines 59 (73 % yield; Scheme ) starting from N , N ‐ bis (methoxymethyl)aniline ( 54 ) and N ‐methoxymethyltetrahydroquinoline ( 57 ), respectively. Both anilines led to in situ formation of the corresponding iminium ion in the presence of TiCl 4 and react with the nucleophilic alkene ethyl vinyl ether.…”

Section: Construction Of the Julolidine Skeletonmentioning

confidence: 99%

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Varejão

Fernandes

2019

Eur J Org Chem

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Julolidines constitute a class of N‐heterocycle compounds which have in common the 2,3,6,7‐tetrahydro‐1H,5H‐benzo[1,2]quinolizine ring. Due mainly to its fluorescence properties, such structures have shown potential application in a range of scientific and technological areas and have attracted attention of a great variety of research groups. For example, julolidines have been used for detection of ions and volatile compounds in environmental and biological samples, to the construction of dye‐sensitized solar cells, photoconductive materials and as fluorescent sensors for bioimaging. This review summarizes the strategies reported to the synthesis of the julolidine ring and the principal modifications for obtaining more complex julolidine derivatives with improved fluorescence properties of these compounds. In this context, aldol condensation, olefination, imine synthesis, and cross‐coupling reactions have been extensively explored and discussed. Examples of applications, which illustrate the great potential of such structures, will also be briefly presented.

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Section: Construction Of the Julolidine Skeletonmentioning

confidence: 99%

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Varejão

Fernandes

2019

Eur J Org Chem

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“…In addition, it was found that Grignard reagents were employed for nucleophilic addition reactions with iminium ions, which indicated the isomerization of iminium ions to enamines in the presence of Grignard reagents could be avoided. 67,68 Based on this information, we planned to employ the magnesium amide enolate of 20 for the Mannich coupling owing to its weaker basicity compared to that of a Li variant. Moreover, the Lewis acidity of Mg has been leveraged for the generation of iminium ions from N,O-acetals.…”

Section: The Mannich Coupling Reaction Of the Northern And Southern Fmentioning

confidence: 99%

Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine

Zhao¹,

Teijaro²,

Chen³

et al. 2018

J. Braz. Chem. Soc.

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It was developed a concise synthetic route resulting in the first syntheses of bis-Strychnos alkaloids (-)-sungucine, (-)-isosungucine, and (-)-strychnogucine B from commercially available (-)-strychnine. Employing a highly convergent synthetic strategy, it was demonstrated that both Strychnos monomers could be efficiently prepared from commercially available (-)-strychnine. The venerable Mannich reaction was enlisted to join the two Strychnos monomers in a biomimetic fashion. Subsequent epimerization and olefin isomerization yielded (-)-strychnogucine B. Functional group manipulation transformed (-)-strychnogucine B into (-)-sungucine and (-)-isosungucine. Computational chemistry was employed to rationalize the regiochemical course of key steps en route to the bis-Strychnos targets.

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“…The α-azidomethylamines also react with ethyl vinyl ether to give tetrahydroquinolines (Scheme 6). 12 Treatment of in situ generated 14 with ethylvinyl ether/ Me 2 AlCl/CH 2 Cl 2 at 0°C gave the adducts 40 (17%) and 41 (58%). Prolonged reaction slowly converted 41 into The ability to selectively functionalize ArNMe 2 groups under very mild conditions, and subsequently conduct Mannich-type chemistry on the NCH 2 N 3 group, has potential applications to the synthesis of heterocycles.…”

Section: Reactions Of Mono-and Bis-azidomethyl Aminesmentioning

confidence: 99%

N-Methyl Azidonation of N,N-Dimethylarylamines with the Iodosylbenzene/Trimethylsilylazide Reagent Combination and some Reactions of α-Azidomethylamines

Magnus¹

1998

Synthesis

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Treatment of N,N -dimethylarylamines with iodosylbenzene/trimethylsilylazide results in functionalization of one of the methyl groups to give the N -azidomethyl derivative. Excess reagent produces the bis-azidomethyl adduct. The azidomethyl group can be hydrolyzed, resulting in overall demethylation. Alternatively, the azide group can be replaced by an alkyl or aryl residue thus providing a new route to unsymmetrical N,N -methylalkylarylamines from a symmetrical starting material.

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Electroorganic chemistry. 62. Reaction of iminium ion with nucleophile: a versatile synthesis of tetrahydroquinolines and julolidines

Cited by 96 publications

References 1 publication

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Synthesis of Bis-Strychnos Alkaloids (–)-Sungucine, (–)-Isosungucine, and (–)-Strychnogucine B from (–)-Strychnine

N-Methyl Azidonation of N,N-Dimethylarylamines with the Iodosylbenzene/Trimethylsilylazide Reagent Combination and some Reactions of α-Azidomethylamines

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