Vilsmeier-Haack Reaction of Phosphonic Dihydrazide: Synthesis of 4- {[(Dimethyl)azanylidenonium Chloride] Methyl} Amino-2,3-Dihydro-3-Oxo-4&lt;i&gt;H&lt;/i&gt;-1,2,4, 3-Triazaphosphole

Ali, Tarik E.; Abdel‐Kariem, Somaia M.

doi:10.5923/j.ijmc.20120205.02

IJMC

2013

DOI: 10.5923/j.ijmc.20120205.02

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Vilsmeier-Haack Reaction of Phosphonic Dihydrazide: Synthesis of 4- {[(Dimethyl)azanylidenonium Chloride] Methyl} Amino-2,3-Dihydro-3-Oxo-4<i>H</i>-1,2,4, 3-Triazaphosphole

Tarik E. Ali¹,

Somaia M. Abdel‐Kariem²

Abstract: A simp le method for the synthesis of 4-{[(dimethyl)azanylidenonium ch loride] methyl}amino-2,3-dihydro-3-o xo -4H-1,2,4,3-t riazaphosphole (2) is described. Treat ment of phosphonic dihydrazide (1 ) with Vilsmeier-Haack reagent led direct ly to the title co mpound in high yield.

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Synthesis and Chemistry of 1,2,4,3-Triazaphosphole Derivatives

Ali

Hassanin

Assiri

et al. 2023

COC

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This review describes the progress made during the last fifty years in the synthesis and chemistry of 1,2,4,3-triazaphospholes. This class of compounds has attracted tremendous homogeneous catalysis and interest in molecular materials science. These fascinating phosphorus heterocycles have conjugated π systems with high degrees of aromaticity. 1,2,4,3-Triazaphospholes can be designed through [3+2] cyclocondensation between functionalized hydrazines with phosphonoimidates that allow the incorporation of additional donor substituents into specific positions of the phosphorus heterocycle. In addition, [4+1] cyclocondensation between functionalized amidrazones and active phosphorus reagents is the most synthetically accessible method. The used strategies facilitated synthetic access to a completely new set of triazaphospholes leading to a much broader scope for potential applications. 1,2,4,3-triazaphospholes displayed reactivity towards a variety of reagents. The phosphorus is particularly prone to undergo oxidative 1,1-addition. Protic reagents such as alcohols, phenols, and amines can be added across the P=N bond of 2H-1,2,4,3-triazaphospholes to yield the dihydro-1,2,4,3-triazaphosphole derivatives. 1H- and 2H-1,2,4,3-triazaphospholes reacted with alcohols, ammonia and amines in the presence of sulfur or selenium to form dihydro-1,2,4,3-triazaphosphole 3-chalcogenides. The appropriate difunctional reagents such as glycols, 2-azido alcohols and phenol with a heterodiene function in the ortho position reacted with 2H-1,2,4,3-triazaphospholes to yield products formed via 1,2-addition on P=N bond. Similar behavior is shown by 2-hydroxyacetophenone and 2-hydroxy-benzophenone. 2H-1,2,4,3-Triazaphospholes reacted with acetylenes to form [3+2] cycloadducts; the latter change to 1,2,3-diazaphospholes. [4+1] Cycloadditions occurred with α-diimines, azodicarboxylic esters, and 1,2-diketones; in the latter two cases, the resulting products dimerize.

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Synthesis and Chemistry of 1,2,4,3-Triazaphosphole Derivatives

Ali

Hassanin

Assiri

et al. 2023

COC

View full text Add to dashboard Cite

show abstract

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Vilsmeier-Haack Reaction of Phosphonic Dihydrazide: Synthesis of 4- {[(Dimethyl)azanylidenonium Chloride] Methyl} Amino-2,3-Dihydro-3-Oxo-4<i>H</i>-1,2,4, 3-Triazaphosphole

Abstract: A simp le method for the synthesis of 4-{[(dimethyl)azanylidenonium ch loride] methyl}amino-2,3-dihydro-3-o xo -4H-1,2,4,3-t riazaphosphole (2) is described. Treat ment of phosphonic dihydrazide (1 ) with Vilsmeier-Haack reagent led direct ly to the title co mpound in high yield.

Cited by 1 publication

References 18 publications

Synthesis and Chemistry of 1,2,4,3-Triazaphosphole Derivatives

Synthesis and Chemistry of 1,2,4,3-Triazaphosphole Derivatives

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