Syntheses, transformations and applications of aminonaphthol derivatives prepared via modified Mannich reactions

Szatmári, István; Fülöp, Ferenc

doi:10.1016/j.tet.2012.11.055

Cited by 74 publications

(49 citation statements)

References 92 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Mechanistically, the bifunctional product is formed by the nucleophilic addition of the electron‐rich aromatic compound on the C=N bond formed by in situ condensation of the aldehyde and amine. As a consequence of the two or more functional groups in the structures of the Mannich bases prepared via such modified reactions, one of the most important areas of application is the synthesis of new heterocycles …”

Section: Introductionmentioning

confidence: 82%

“…A special variation of this latter reaction when formaldehyde is replaced by benzaldehyde, the secondary amine by ammonia, and the C−H acid by an electron‐rich aromatic compound such as 2‐naphthol. The reaction was first developed by Mario Betti and the aminonaphthol synthesized in this way became as Betti base . This modified three‐component Mannich reaction (mMR) was then extended to apply 1‐naphthol, quinolinol or isoquinolinol as electron‐rich aromatic compounds .…”

Section: Introductionmentioning

confidence: 99%

“…The reaction was first developed by Mario Betti and the aminonaphthol synthesized in this way became as Betti base . This modified three‐component Mannich reaction (mMR) was then extended to apply 1‐naphthol, quinolinol or isoquinolinol as electron‐rich aromatic compounds . Mechanistically, the bifunctional product is formed by the nucleophilic addition of the electron‐rich aromatic compound on the C=N bond formed by in situ condensation of the aldehyde and amine.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Ortho‐Quinone Methide Driven Synthesis of New O,N‐ or N,N‐Heterocycles

et al. 2019

Self Cite

View full text Add to dashboard Cite

To synthesize functionalized Mannich bases that can serve two different types of ortho ‐quinone methide ( o ‐QM) intermediates, 2‐naphthol and 6‐hydroxyquinoline were reacted with salicylic aldehyde in the presence of morpholine. The Mannich bases that can form o ‐QM and aza ‐ o ‐QM were also synthesized by mixing 2‐naphthol, 2‐nitrobenzaldehyde, and morpholine followed by reduction of the nitro group. The highly functionalized aminonaphthol derivatives were then tested in [4+2] cycloaddition with different cyclic imines. The reaction proved to be both regio‐ and diastereoselective. In all cases, only one reaction product was obtained. Detailed structural analyses of the new polyheterocycles as well as conformational studies including DFT modelling were performed. The relative stability of o ‐QMs/ aza‐o ‐QM were also calculated, and the regioselectivity of the reactions could be explained only when the cycloaddition started from aminodiol 4 . It was summarized that starting from diaminonaphthol 25 , the regioselectivity of the reaction is driven by the higher nucleophilicity of the amino group compared with the hydroxy group. 12H‐benzo[a]xanthen‐12‐one ( 11 ), formed via o ‐QM formation, was isolated as a side product. The proton NMR spectrum of 11 proved to be very unique from NMR point of view. The reason for the extreme low‐field position of proton H‐1 could be accounted for by theoretical calculation of structure and spatial magnetic properties of the compound in combination of ring current effects of the aromatic moieties and steric compression within the heavily hindered H(1)‐C(1)‐C(12b)‐C(12a)‐C(12)=O structural fragment.

show abstract

Section: Introductionmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Ortho‐Quinone Methide Driven Synthesis of New O,N‐ or N,N‐Heterocycles

et al. 2019

Self Cite

View full text Add to dashboard Cite

show abstract

“…Previously, some papers [14][15][16][17][18][19] reported the Betti reaction as a route for the asymmetric synthesis of chiral nonracemic amino benzylnaphthols. This procedure is a straightforward condensation of 2-naphthol, aryl aldehydes and suitable chiral nonracemic amines (Schemes 1 and 2) to yield more complex molecular structures.…”

Section: Introductionmentioning

confidence: 99%

Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans

et al. 2014

View full text Add to dashboard Cite

Chiral nonracemic aminobenzylnaphthols were obtained by a Betti multicomponent reaction between 2-naphthol, aryl aldehydes and enantiopure arylethylamine. Moreover, some new aminobenzylnaphthols were synthesized by a similar reaction between 2-naphthol, aryl aldehydes and prolinol. These aminobenzylnaphthols, synthesized from different components and thus having different structural features, were tested as anti-yeast agents inhibiting Candida albicans. The effect towards the test strain was studied with a microdilution approach and three different concentrations (150, 300 and 450 µg/mL) were tested. The best results were found for the aminobenzylnaphthols obtained from 1-naphthylethylamine and from natural prolinol. The use of the two-way ANOVA highlighted the better performances of the prolinol derivative among the differently structured aminobenzylnaphthols that were screened. The activity towards C. albicans of this prolinol derivative resulted to be interesting and could represent a promising alternative to overcome the problem of the strains resistant to the traditional antifungals.

show abstract

“…This protocol is known as Betti reaction and the compound formed as Betti base [7–9]. Several examples have been published to extend the reaction and to synthesize varied substituted aminonaphthol derivatives [10]. Their relatively easy accessibility and promising biological properties have led to the resurgence of their chemistry coming again into the focus of pharmacological research.…”

Section: Introductionmentioning

confidence: 99%

Mannich base-connected syntheses mediated by ortho-quinone methides

Barta¹,

Fülöp²,

Szatmári³

2018

Beilstein J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

This article provides an overview about specifically modified Mannich reactions where the process involves an ortho-quinone methide (o-QM) intermediate. The reactions are classified on the basis of the o-QM source followed by the reactant, e.g., the dienophile partner in cycloaddition reactions (C=C or C=N dienophiles) or by the formation of multicomponent Mannich adducts. Due to the important pharmacological activities of these reactive o-QM intermediates, special attention is paid to the biological activity of these compounds.

show abstract

Syntheses, transformations and applications of aminonaphthol derivatives prepared via modified Mannich reactions

Cited by 74 publications

References 92 publications

Ortho‐Quinone Methide Driven Synthesis of New O,N‐ or N,N‐Heterocycles

Ortho‐Quinone Methide Driven Synthesis of New O,N‐ or N,N‐Heterocycles

Bioactivity of a Family of Chiral Nonracemic Aminobenzylnaphthols towards Candida albicans

Mannich base-connected syntheses mediated by ortho-quinone methides

Contact Info

Product

Resources

About