Amino(hetero)arylmethylation of Phenols with <i>N</i>-[α-Amino(hetero)arylmethyl]benzotriazoles

Katritzky, Alan R.; Abdel‐Fattah, Ashraf A. A.; Tymoshenko, Dmytro O.; Belyakov, S. A.; Ghiviriga, and Ion; Steel, Peter J.

doi:10.1021/jo9903609

Cited by 41 publications

(14 citation statements)

References 21 publications

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“…Although the Mannich bases of 2-naphthols with heterocyclic amines were reported in the past (24, 26, 27, 51), their detailed NMR behavior has not been examined, to the best of our knowledge; some NMR peaks are reported in broad range (27). We consistently noted interesting NMR activities of the compounds under investigation, as they often gave poorly resolved heterocyclic proton and carbon peaks in their respective spectra at ambient temperature.…”

Section: Resultsmentioning

confidence: 61%

“…The first synthesis of racemic Mannich bases of 2-naphthol was achieved by Betti (18)(19)(20)(21)(22) at the turn of the 20th century. Thereafter, numerous modifications of this reaction surfaced (23)(24)(25)(26)(27) and optically pure Betti base analogs were prepared either by resolution or by the induction of chirality by the use of optically active amines (11-17, 28, 29).…”

Section: Introductionmentioning

confidence: 99%

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Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour

Jha¹,

Paul²,

Trikha³

et al. 2006

Can. J. Chem.

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A novel two-step procedure involving the formation of 1-arylidene-2-tetralones from 2-tetralone and subsequent Michael addition of a cyclic secondary amine on the alkenone followed by in situ aerial oxidation was developed to produce 2-naphthol Mannich bases. A simple microwave-assisted one-pot synthesis of 2-naphthol Mannich bases was also carried out under solvent-free conditions from 2-naphthol and corresponding aldehydes and amines in the presence of p-toluenesulfonic acid. The compounds of this series displayed interesting NMR behaviour. Extensive variabletemperature NMR investigations, including HSQC experiments, are herein reported. NMR results on the conformation in solution phase were found to be consistent with the X-ray crystal structure in the solid state.Résumé : On a mis au point une nouvelle méthode en deux étapes qui permet de produire des bases de Mannich du 2-naphtol et qui implique la formation de 1-arylidène-2-tétralones à partir de la 2-tétralone, puis une addition subséquente de Michael d'une amine secondaire cyclique sur l'alcénone, suivie d'une oxydation in situ par de l'air. On a aussi réa-lisé une synthèse des bases de Mannich du 2-naphtol par une simple réaction monotope du 2-naphtol, des aldéhydes et des amines correspondants en présence d'acide p-toluènesulfonique, sous l'effet de micro-ondes, dans des conditions sans solvant. Les composés de cette série présentent des comportements RMN intéressants. On a effectué de nombreuses études RMN à température variable, y compris des expériences de « HSQC ». On a trouvé que les résultats de la RMN sur la conformation en solution sont en accord avec la structure cristalline déterminée par diffraction des rayons X, à l'état solide.Mots clés : bases de Mannich, réaction de Mannich assistée par les micro-ondes, spectroscopie RMN à température variable, dynamique RMN, cristallographie par diffraction des rayons X.[Traduit par la Rédaction] Jha et al. 853

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Section: Resultsmentioning

confidence: 61%

Section: Introductionmentioning

confidence: 99%

Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour

Jha¹,

Paul²,

Trikha³

et al. 2006

Can. J. Chem.

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“…Katritzky et al 3 have reported an improved aminoalkylation of 2-naphthol and phenol derivatives with prefor med iminium salts derived from aromatic aldehydes, in a two-step sequence with 26%-92% yields. Moreover, aminoalkylation of electron rich aromatic compounds such as 2-naphthol for the synthesis of Betti base derivatives [4][5][6][7][8][9][10][11][12][13][14] in the presence of LiClO 4 , Sc(OTf) 3 , Yb(OTf) 3 , La(OTf) 3 , YbCl 3 , TiCl 4 and Me 3 SiCl as catalysts has been reported. [15][16][17] The racemic aminonaphthols (Betti bases) have been used for transformation into products with anti bacterial activity.…”

Section: Introductionmentioning

confidence: 99%

Convenient and Efficient Method for the Synthesis of N‐Heteroaryl Aminonaphthols under Solvent‐Free Conditions

Olyaei¹,

Raoufmoghaddam

Sadeghpour

et al. 2010

Chin. J. Chem.

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A convenient, efficient and green synthesis of N-heteroaryl aminonaphthols has been developed by one-pot, three-component condensation of β-naphthol, heteroaryl amines and substituted benzaldehydes under solvent-free conditions at elevated temperature. The advantages of these reactions are simplicity of the reaction procedure, short reaction times, simple work-up, catalyst-free conditions and pure products in good to excellent yields.

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“…The first synthesis of racemic Mannich-bases of 2-naphthol was achieved by Betti at the turn of the twentieth century. 4 Thereafter numerous modifications of this reaction surfaced [5][6][7][8][9][10] . Since these compounds have multiple centers for chelation with metal ions, they are likely to be potent inhibitors of metallo-enzymes 11,12 .…”

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confidence: 99%