Convenient Synthesis of New Boric Acid Catalyzed 1,2,4‐Triazolopyridinone Derivatives and an Investigation of their Optical Properties

Darehkordi, Ali; Hosseini, Marjan; Rahmani, Fariba

doi:10.1002/jhet.3501

Cited by 7 publications

(7 citation statements)

References 29 publications

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“…The reaction of 1,6-diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile 18 with ninhydrin ( 19 ) in acetic acid catalyzed by boric acid produced dihydroindeno[1,2- e ]pyrido[1,2- b ][1,2,4]triazine-1,3- dicarbonitriles 20 in moderate to excellent yield. 13…”

Section: Table 1 Recent Applications Of Boric Acid In O...mentioning

confidence: 99%

Boric Acid: A Mild and Efficient Green Catalyst for Organic Transformations

Rawat¹,

Kumar²,

Kumar³

et al. 2023

SynOpen

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The acid catalyzed reaction is one of the most important reactions in organic chemistry. Most acid catalyzed reactions have been studied in the presence of strong acids such as H2SO4, HNO3, HCl, BF3.O(Et)2, TFA, and methanesulfonic acid etc. in various organic solvents. The use of excessive and even stoichiometric amounts of acids with organic solvents raises environmental concerns. To avoid the use of corrosive acids and to reduce the environmental impact, the development of a new method for organic synthesis catalyzed by boric acid would be highly desirable. The benefits and uses of boric acid-catalyzed reactions were covered in this communication.

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Section: Table 1 Recent Applications Of Boric Acid In O...mentioning

confidence: 99%

Boric Acid: A Mild and Efficient Green Catalyst for Organic Transformations

Rawat¹,

Kumar²,

Kumar³

et al. 2023

SynOpen

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“…39 Boric acid has also been shown to effectively promote the condensation of ninhydrin with 1,6diamino-2-oxo-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitriles to form highly substituted 1,2,4-triazolopyridinones with interesting near-infrared emission spectra (Scheme 4). 40 Diaryl borinic acids bearing strong electron-withdrawing groups, typically fluoro groups, have been found to be effective for the selective dehydration of β-hydroxy carbonyl compounds produced from Mukaiyama aldol reactions. 24 The borinic acid proved effective at promoting the dehydration where standard Brønsted acids failed to give the desired Representative reactions that are catalyzed by organoboron acids: dehydration, 24 carbonyl condensation, 25 acylation, 26 alkylation, 27 and cycloaddition.…”

Section: ■ Dehydrationmentioning

confidence: 99%

Emergent Organoboron Acid Catalysts

Graham

Raines

2022

J. Org. Chem.

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Organoboron acids are stable, organic-soluble Lewis acids with potential application as catalysts for a wide variety of chemical reactions. In this review, we summarize the utility of boronic and borinic acids, as well as boric acid, as catalysts for organic transformations. Typically, the catalytic processes exploit the Lewis acidity of trivalent boron, enabling the reversible formation of a covalent bond with oxygen. Our focus is on recent developments in the catalysis of dehydration, carbonyl condensation, acylation, alkylation, and cycloaddition reactions. We conclude that organoboron acids have a highly favorable prospectus as the source of new catalysts.

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“…13 The majority of the new reported methods for the construction of pyrido [1,2,4]-triazines, use reactions of 4-aryl-1,6-diamino-2oxo-1,2-dihydro-pyridine-3,5-dicarbonitrile derivatives as a precursor with some active dicarbonyl compounds in the presence of a catalyst. [14][15][16] Diversity-Oriented Synthesis (DOS) is a new approach consists of synthetic methods to generating and developing new chemical diverse compounds libraries. 17 DOS explores some promising new applications, that have the potential to signicantly advance studies in drug discovery and chemical biology, so that increase the biological outcome of the molecules.…”

Section: Introductionmentioning

confidence: 99%