Solvent-free Synthesis of 2,4,6-Triarylpyridine Derivatives Promoted by 1,3-Dibromo-5,5-dimethylhydantoin

doi:10.1080/00304948.2015.1005990

Paper

Solvent-free Synthesis of 2,4,6-Triarylpyridine Derivatives Promoted by 1,3-Dibromo-5,5-dimethylhydantoin

Published Mar 4, 2015 · B. Maleki

Organic Preparations and Procedures International

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Abstract

The development of new methods for the synthesis of 2,4,6-triarylpyridines is an important area of research because of the broad spectrum of their biological and pharmaceutical properties such as anti-covulsant, anesthetic, anti-malarial, vasodilator, anti-epileptic character and their use as pesticidial, fungicidal and herbicidal agro-chemicals. Due to their p-stacking ability, some pyridines are used in supramolecular chemistry. The 2,4,6-triarylpyridine nucleus is structurally related to symmetrical triarylthio-, triarylselenoand triaryltelluoropyrylium salt photosensitizers and has been recommended for photodynamic cell–specific cancer therapy. This wide range of applications has elicited several methods for their prepa-ration. 22 Among these, the one-pot reaction of aromatic ketones or aldehydes with ammonium acetate is one of the simplest and most straightforward approaches. A variety of reagents such as PEG-400, HClO4.SiO2, 24 H14[NaP5W30O110], 25 molecular iodine, microwave irradiation without catalyst, [BmIm][BF4], wet 2,4,6-trichloro-1,3,5-triazine (TCT), pentafluorophenylammonium triflate, trichloroisocyanuric acid, bismuth triflate, and MgAl2O4 nanocrystals 33 have been employed to promote this transformation. Some of these procedures involve the use of strong corrosive acids or bases, solvents, microwave irradiation, metal salts, high catalyst loading and tedious work-up. Thus the development of a new readily available method that avoids many of these problems is highly desirable. In recent years, 1,3-dibromo-5,5-dimethylhydantoin (DBH) has been used as a cata-lyst for a number of reactions because it is relatively inexpensive, non-toxic, quite stable and easy to handle. We now report the preparation of 2,4,6-triarylpyridines from aldehydes and acetophenones by treatment with ammonium acetate in the presence of catalytic amounts of 1,3-dibromo-5,5DBH under solvent-free conditions (Scheme 1).

Study Snapshot

This study presents a solvent-free method for preparing 2,4,6-triarylpyridine derivatives from aldehydes and acetophenones, offering potential for biological and pharmaceutical applications.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Solvent-free Synthesis of 2,4,6-Triarylpyridine Derivatives Promoted by 1,3-Dibromo-5,5-dimethylhydantoin

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Citations

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