Recent advances in the synthesis of 5'-deoxynucleoside phosphonate analogs

2021 ◽  
Vol 28 ◽  
Author(s):  
Guang Huan Shen ◽  
Joon Hee Hong
Keyword(s):  
Biological Activity ◽  
Radical Reaction ◽  
Cross Coupling ◽  
Mitsunobu Reaction ◽  
Addition Reactions ◽  
Arbuzov Reaction ◽  
Displacement Reaction ◽  
Cross Metathesis ◽  
Nucleophilic Displacement ◽  
Vinyl Phosphonates

: The present review focuses on the synthesis of cyclic 5-deoxynucleoside phosphonate analogs. The formation of various phosphonate alkyl moieties is accomplished through (i) Wittig (or HWE) type condensation to the nucleoside aldehyde moiety; (ii) nucleophilic displacement reaction using phosphonate anion or Lewis acid; (iii) Arbuzov reaction; (iv) olefin cross-metathesis between vinyl phosphonates and vinylated nucleosides; and (v) radical reaction and Pd catalyzed alkyne. For the coupling of nucleobases with cyclic moieties, the Mitsunobu reaction, and Sonogashira-type cross-coupling are usually applied. For the coupling of furanose moieties with nucleobases, Vorbrüggen-type condensation is generally applied. Addition reactions mediated by selenium ions are mainly applied for the coupling of carbocyclic moieties. Their biological activity results are summarized.

A Revised Modular Approach to D8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
One Pot ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Chemistry Research

<p>In this manuscript we describe a modular pathway to synthesize biologically relevant (–)-<i>trans</i>-Δ<sup>8</sup>-THC derivatives, which can be used to modulate the pharmacologically important CB<sub>1</sub> and CB<sub>2</sub> receptors. This pathway involves a one-pot Friedel-Crafts alkylation/cyclization protocol, followed by Suzuki-Miyaura cross-coupling reactions and gives rise to a series of new Δ<sup>8</sup>-THC derivatives. In addition, we demonstrate using extensive NMR evidence that similar halide-substituted Friedel-Crafts alkylation/cyclization products in previous articles were wrongly assigned as the para-isomers, which also has consequence for the assignment of the subsequent cross-coupled products and interpretation of their biological activity. </p> <p>Considering the importance of the availability of THC derivatives in medicinal chemistry research and the fact that previously synthesized compounds were wrongly assigned, we feel this research is describing a straightforward pathway into new cannabinoids.</p>

scholarly journals Synthesis of 2-Alkenyl-Tethered Anilines

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2873-2888 ◽  
Author(s):  
Scott Denmark ◽  
Hyung Chi
Keyword(s):  
Lewis Acid ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Cope Rearrangement ◽  
The Third ◽  
Cross Metathesis ◽  
Direct Cross ◽  
Palladium Catalyzed

Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N-allylic anilines in the presence of a Lewis acid. The requisite N-allylic anilines were prepared by the addition of vinylmagnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C–N cross-coupling of aryl halides. Taken together, these three strategies allowed access to the requisite aniline substrates with pendant alkenes at the 2-position with excellent trans selectivities.

A General Approach to Selective Functionalization of 1,2,4-Triazines Using Organometallics in Palladium-Catalyzed Cross-Coupling and Addition Reactions.

ChemInform ◽  
2005 ◽  
Vol 36 (17) ◽  
Author(s):  
France-Aimee Alphonse ◽  
Franck Suzenet ◽  
Anne Keromnes ◽  
Bruno Lebret ◽  
Gerald Guillaumet
Keyword(s):  
Cross Coupling ◽  
Addition Reactions ◽  
Selective Functionalization ◽  
Palladium Catalyzed

scholarly journals Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Masakazu Nambo ◽  
Jacky C.-H. Yim ◽  
Luiza B. O. Freitas ◽  
Yasuyo Tahara ◽  
Zachary T. Ariki ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Recent Progress ◽  
Cross Coupling ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Arylboronic Acids ◽  
Modular Synthesis ◽  
Synthetic Routes

Abstract α-Fluoromethylarenes are common substructures in pharmaceuticals and agrochemicals, with the introduction of fluorine often resulting in improved biological activity and stability. Despite recent progress, synthetic routes to α-fluorinated diarylmethanes are still rare. Herein we describe the Pd-catalyzed Suzuki-Miyaura cross-coupling of α-fluorinated benzylic triflones with arylboronic acids affording structurally diverse α-fluorinated diarylmethanes. The ease of synthesis of fluorinated triflones as the key starting materials enables powerful late-stage transformations of known biologically active compounds into fluorinated analogs.

Reactions in microemulsion media. Nucleophilic displacement reaction of benzyl chloride with bromide ion

1982 ◽  
Vol 23 (45) ◽  
pp. 4651-4654 ◽  
Author(s):  
Craig A. Martin ◽  
Patrick M. MgCrann ◽  
George H. Angelos ◽  
David A. Jaeger
Keyword(s):  
Benzyl Chloride ◽  
Displacement Reaction ◽  
Nucleophilic Displacement ◽  
Bromide Ion

scholarly journals One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

2015 ◽  
Vol 11 ◽  
pp. 1265-1273 ◽  
Author(s):  
Mohammad Abbasi ◽  
Reza Khalifeh
Keyword(s):  
Conjugate Addition ◽  
Alkyl Halides ◽  
Displacement Reaction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Organic Halides ◽  
Nucleophilic Displacement ◽  
In Situ Generation

An efficient and odourless procedure for a one-pot synthesis of thioesters by the reaction of benzoic anhydrides, thiourea and various organic halides (primary, allylic, and benzylic) or structurally diverse, electron-deficient alkenes (ketones, esters, and nitriles) in the presence of Et3N has been developed. In this method, thiobenzoic acids were in situ generated from the reaction of thiourea with benzoic anhydrides, which were subjected to conjugate addition with electron-deficient alkenes or a nucleophilic displacement reaction with alkyl halides.

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