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. 2014 Nov 22;9(4):e17808.
doi: 10.17795/jjnpp-17808. eCollection 2014 Nov.

Solvent-free preparation of novel 2-[phenyl (pyridine-2-ylamino) methyl] phenols as pseudo-betti processor for natural products

Mohammad Reza Shushizadeh  1 , Somaye Azizyan  2
Affiliations

Solvent-free preparation of novel 2-[phenyl (pyridine-2-ylamino) methyl] phenols as pseudo-betti processor for natural products

Mohammad Reza Shushizadeh et al. Jundishapur J Nat Pharm Prod. .

Abstract

Background: 2-Aminopyridine and benzaldehydes mixture readily reacted with phenols at 80°C without any solvents to produce novel 2-[phenyl (pyridine-2-yl amino (methyl] phenol derivatives as pseudo-Betti products in good to high yields. These compounds are efficient processor for synthesis of the natural products.

Objectives: We decided to report the synthesis of a series of novel N-heteroaryl-arylmethyl phenols via a simple three-component, one-pot method, using aromatic aldehydes, heteroaryl amines, and phenols in the absence of any acid catalysts and under solvent-free conditions.

Materials and methods: All starting materials were purchased from Merck and Aldrich companies. The IR spectra were recorded on a Perkin-Elmer RXI infrared spectrometer.

Results: The reaction is convenient, operationally simple, proceeds quickly, and does not need solvents or expensive starting materials. The structures of the products were characterized by their spectral (1H NMR and IR) data.

Conclusions: We have developed a new, simple, and efficient method for one-pot aminoalkylation of active phenol compounds with various imines prepared from 2-aminopyrimidine and benzaldehydes in good to high yields (40%-97%).

Keywords: 2-Amino pyridine; Base; Phenols; Pseudo-Betti; Solvent-Free.

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Figures

Figure 1.
Figure 1.. One-Pot Synthesis of Hetero-aminoalkyl Phenols
Figure 2.
Figure 2.. Mechanism of amino alkyl Phenols Synthesis
See this image and copyright information in PMC

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