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

Waes, Frederik E. A. Van; Debrouwer, Wouter; Heugebaert, Thomas S. A.; Stevens, Christian V.

doi:10.3998/ark.5550190.p008.648

Cited by 8 publications

(2 citation statements)

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“…After a theoretical study and the rationalization of the the authors concluded that the differences of depend on the influence of the position of the nitrogen atoms in the (poly)aromatic compounds and the affinity toward protonation at a nitrogen atom. 357,358 5.2.3. Dihydroisoquinolines.…”

Section: Tetrahydroisoquinolines and Tetrahydroquinolinesmentioning

confidence: 99%

“… With some variations, this methodology was applied for the diphosphonylation of 1,5-naphthyridine and several phenanthrolines, which react only under MW heating. After a theoretical study and the rationalization of the experimental evidence, the authors concluded that the differences of reactivity depend on the influence of the position of the nitrogen atoms in the (poly)aromatic compounds and the affinity toward protonation at a nitrogen atom. , …”

Section: Six-membered Rings: Nonaromatic Aromatic and Benzo-fused Het...mentioning

confidence: 99%

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

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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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.

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Section: Tetrahydroisoquinolines and Tetrahydroquinolinesmentioning

confidence: 99%