New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP)

Viveros‐Ceballos, José Luis; Matías-Valdez, Lizeth A; Sayago, Francisco J.; Cativiela, Carlos; Ordóñez, Mario

doi:10.1007/s00726-021-02962-4

Cited by 7 publications

(4 citation statements)

References 58 publications

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“…Possible alternatives for the commonly used CDC-type reactions can be found in the work of Ordóñez et al, here the authors describe the use of a Kabachnik–Fields and/or aza-Pudovik reaction on readily available substrates for the synthesis of 1-phosphonylated tetrahydroisoquinolines 591 in excellent yields . Shortly after, the same group presented two strategies for the synthesis of 1,2,3,4-tetrahydroisoquinoline-3-phosphonic acid using a Wittig–Horner or Pictet–Spengler reaction . Additionally, Guo and co-workers recently published an enantioselective chiral phosphoric acid catalyzed dearomatization of isoquinolines, which leads to the closely related 1,2-dihydroisoquinoline phosphonates in moderate to excellent yields and enantioselectivities …”

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

confidence: 99%

“…347 Shortly after, the same group presented two strategies for the synthesis of 1,2,3,4-tetrahydroisoquinoline-3phosphonic acid using a Wittig−Horner or Pictet−Spengler reaction. 348 Additionally, Guo and co-workers recently published an enantioselective chiral phosphoric acid catalyzed dearomatization of isoquinolines, which leads to the closely related 1,2-dihydroisoquinoline phosphonates in moderate to excellent yields and enantioselectivities. 349 A protocol free of metals, additives, or the need for photo-or electrochemical activation was published by Prabhu and collaborators.…”

Section: Tetrahydroisoquinolines and Tetrahydroquinolinesmentioning

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

confidence: 99%

Section: Tetrahydroisoquinolines and Tetrahydroquinolinesmentioning

confidence: 99%

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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“…Ceballos et al reported the synthesis of tetrahydroisoquinoline-3-phosphonic acid (±)- 325 (Scheme 67). 112 Wittig–Horner olefination of N -Cbz protected α-aminomethylene bisphosphonate 322 with benzaldehyde and electron-transfer reduction furnishes N -Cbz phosphonophenylalanine diethyl ester (±)- 323 . Pictet–Spengler cyclization of 323 followed by hydrolysis with HBr affords THIQ 325 .…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

Vijayakumar,

Manod,

Krishna

et al. 2023

RSC Med. Chem.

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“…The tandem decarboxylation-phosphorylation process was recently adapted by Viveros-Ceballos et al (2021) to prepare tetrahydroisoquinoline-3-phosphonic acids, which are key components of enzyme inhibitors and other bioactive products. In another example, nucleotide analogs were formed by a decarboxylation-phosphorylation reaction ( Miguélez et al, 2013b ).…”

Section: Oxidative O -Radical Scission-addition Of...mentioning

confidence: 99%

“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles

et al. 2022

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Hypervalent iodine reagents have been applied in many metal-free, efficient synthesis of natural products and other bioactive compounds. In particular, treatment of alcohols, acetals and acids with hypervalent iodine reagents and iodine results in O-radicals that can undergo a β-scission reaction. Under these oxidative conditions, derivatives of amino acids, peptides or carbohydrates are converted into cationic intermediates, which can subsequently undergo inter- or intramolecular addition of nucleophiles. Most reported papers describe the addition of oxygen nucleophiles, but this review is focused on the addition of carbon, nitrogen and phosphorous nucleophiles. The resulting products (nucleoside and alkaloid analogs, unnatural amino acids, site-selectively modified peptides) are valuable intermediates or analogs of bioactive compounds.

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New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP)

Cited by 7 publications

References 58 publications

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

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

Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry

“Cut and Paste” Processes in the Search of Bioactive Products: One-Pot, Metal-free O-Radical Scission-Oxidation-Addition of C, N or P-Nucleophiles

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