A convenient route to novel fluorinated 1,2,4,3-triazaphospholo[1,5-a]pyridines and pyrido[1,2-b][1,2,4,5]triazaphosphinines

Abstract

A simple synthetic approach to the construction of novel fluorinated 5-oxo(thioxo)-2-oxido(sulfido)-1,2,4,3triazaphospholo [1,5-a]pyridines 2-14 and pyrido [1,2-b][1,2,4,5]triazaphosphinines 16, 19 and 22, was achieved. The method depends on the treatment of 1,6-diamino-4-(4-fluorophenyl)-2-oxo-1,2dihydropyridine-3,5-dicarbonitrile (1) with some different types of phosphorus reagents such as phosphorus acid, and their esters, phosphorus halides as well as phosphorus sulfides. Structures of all the synthesized products were established by elemental analysis and spectral tools.

Synthesis of Novel 2-diethylamino-4H-7-(Het) aryl pyrido[1,2-a][1,3,5]triazin-4-ones via a Suzuki Cross-Coupling Reaction of 2-Diethylamino-4H-7-iodopyrido[1,2a][1,3,5]triazin-4-one with (Het) arylboronic Acids in Water

“…It is interesting that replacing hydrogen and other functional groups with fluorine atoms can have a dramatic effect on the modulation of electronic, lipophilic, and steric parameters, all of these can critically influence both the pharmacodynamic and pharmacokinetic properties of drugs. Based upon these results, the present overview reports an important route of fluorine compounds substituted 1,3,5-triazine with the study of chemical reactivities and evaluation of the effects on the vital biological process [43].…”

Methylene Components Exchange in the Reaction of Cyanoacetohydrazide with 2-Amino-4-arylbuta-1,3-diene-1,1,3-tricarbonitriles

“…The reaction of cyanoacetohydrazide 1 with α,βunsaturated nitriles 2 or aldehydes and methylene active nitriles 3 (in a multicomponent version) leads to the formation of 1,6-diamino-2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives 4 [1][2][3][4][5][6] (Scheme 1). Such compounds are of interest as starting materials for the preparation of polyazaheterocycles with a bridging nitrogen atom, namely fused 1,2,4-triazines 5 [7,8], 1,2,4,3-triazaphospholo [1,5-a]pyridines 6 [9], [1,2,4]triazolo [1,5-a]pyridines 7 [10][11][12], pyrido [1,2-b] [1,2,4]triazepines 8 [13][14][15][16], and nicotinonitrile derivatives 9 [3] (Scheme 1). Compounds 4 are also promising lowmolecular-weight ligands with an antitumor effect for binding VEGFR-2 kinase [17], phosphodiesterase PDE4 [18], new antibacterial and fungicidal drugs [19], etc.…”

Synthetic of Some New Fluorine Compounds Bearing 1,2,4-Triazine Moieties and the Related Hetero-Polycyclic Nitrogen Systems as Pharmacological Probes-Overview

“…Most of the studies addressing synthesis and chemistry of fluorinated hetero-cyclic have been related to drug discovery research [9] [10]. It is interesting that replacing hydrogen and other functional groups with fluorine atoms can have a dramatic effect on the modulation of electronic, lipophilic, and steric parameters, all of which can critically influence both the pharmacodynamic and pharmacokinetic properties of drugs.…”