Synthesis of N-vinyl 2,2-bisphosphonoaziridines from 1,1-bisphosphono-2-aza-1,3-dienes

Mortier, Pieter P. J.; Waes, Frederik E. A. Van; Masschelein, Kurt G. R.; Heugebaert, Thomas S. A.; Stevens, Christian V.

doi:10.1016/j.tetlet.2011.05.149

Cited by 11 publications

(6 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…During our ongoing research on the use of heteroatom transfer radical cyclization (HATRC) for the design of phosphonylated heterocycles, − an unexpected synthesis of diethyl (2-phenyl-3-azabicyclo[3.1.0]hexan-1-yl)phosphonates 1 (Figure ) has been elaborated. Bicyclic β-aminophosphonates bearing a phosphonate moiety at the bridgehead of the bicyclic structure have only scarcely been reported in literature. − …”

Section: Introductionmentioning

confidence: 99%

Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes

et al. 2013

Self Cite

View full text Add to dashboard Cite

3-Azabicyclo[3.1.0]hex-2-en-1-yl phosphonates were prepared in a five-step reaction route from β-ketophosphonates. The key steps in this sequence are an atom-transfer radical cyclization and an unforeseen lithium-halogen exchange with n-BuLi. The cyclization reaction proceeds with excellent diastereoselectivity. The resulting cyclic imines were reduced, and 3-azabicyclo[3.1.0]hexan-1-yl phosphonates were obtained.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes

et al. 2013

Self Cite

View full text Add to dashboard Cite

show abstract

“…The best results were obtained under reflux conditions (entry 22). Performing the reaction in a higher boiling solvent (entries [25][26] or with more H 2 SO 4 (entry 23) had no beneficial effect on the conversion. The product formed could be isolated and was identified as the methylated monoaddition product of P(OMe) 2 OTMS to ftalazine: dimethyl (2-methyl-1,2-dihydroftalazine-1-yl)phosphonate.…”

Section: Other Aromatic Heterocyclesmentioning

confidence: 98%

On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes

Waes¹,

Debrouwer²,

Heugebaert³

et al. 2014

Arkivoc

Self Cite

View full text Add to dashboard Cite

Over the past 15 years we have developed a one-step protocol for the synthesis of 3-phosphonylated aminophosphonates from α,β-unsaturated imines through tandem 1,4-1,2-phosphite addition. This account covers the initial development, mechanistic implications of using different phosphite nucleophiles and the expansion towards oximes, hydrazones and unsaturated imines included in aromatic sextets, e.g. quinolines, phenanthrolines and napthyridines.

show abstract

“…Other diazo reagents, such as ethyl diazoacetate and trimethylsilyl(diazomethane), were unable to perform the conversion. 82 Instead of performing a reaction between a diazo compound and a phosphonylated azadiene, as shown in the previous examples, phosphonylated diazo compound can also be used. Bartnik and co-workers used diethyl diazomethylphosphonate (44) in combination with 1,3,5-triaryl-hexahydro-1,3,5-triazine (45).…”

Section: )mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

Self Cite

View full text Add to dashboard Cite

The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search in the development of synthetic routes for obtaining novel members of this family of compounds. This updated review covers methodologies established since 2004, focusing on the synthesis of azaheterocyclic phosphonates, of which the phosphonate moiety is directly substituted onto to the azaheterocyclic structure. Emphasizing recent advances, this review classifies newly developed synthetic approaches according to the ring size and providing information on biological activities whenever available. Furthermore, this review summarizes information on various methods for the formation of C–P bonds, examining sustainable approaches such as the Michaelis–Arbuzov reaction, the Michaelis–Becker reaction, the Pudovik reaction, the Hirao coupling, and the Kabachnik–Fields reaction. After analyzing the biological activities and applications of azaheterocyclic phosphonates investigated in recent years, a predominant focus on the evaluation of these compounds as anticancer agents is evident. Furthermore, emerging applications underline the versatility and potential of these compounds, highlighting the need for continued research on synthetic methods to expand this interesting family.

show abstract

Synthesis of N-vinyl 2,2-bisphosphonoaziridines from 1,1-bisphosphono-2-aza-1,3-dienes

Cited by 11 publications

References 27 publications

Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes

Synthetic Entry into 1-Phosphono-3-azabicyclo[3.1.0]hexanes

On the discovery and development of tandem 1,4- and 1,2-addition of phosphites to 1-azadienes

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Contact Info

Product

Resources

About