Expedient synthesis of 2-alkylthio-<i>N</i><sup>6</sup>-aryladenosines from guanosine

Tian, Mingzhen; Chen, Ning; Xu, Fangming; Li, Xiuxiu; Li, Shunlai; Du, Hongguang

doi:10.1080/17415993.2017.1391812

Cited by 4 publications

(1 citation statement)

References 22 publications

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“…Purines are one class of the most important and attractive compounds due to their unique structure and irreplaceable biological activities [48–51] . The modification of the purine skeleton is our continuous interest [52–55] . Since 6‐chloropurines have been developed as effective electrophiles toward various amides and alcohols, we thus envisioned that it could also be activated by DMSO to afford the corresponding oxosulfonium intermediates B , which might further rearrange to give N ‐MTM derivatives.…”

Section: Introductionmentioning

confidence: 99%

N¹‐Methylthiomethylation of (8‐Aza)6‐Chloropurine with DMSO through the Pummerer Rearrangement

Wang

Chen

2023

ChemistrySelect

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N1‐[(Methylthio)methyl] hypoxanthines and aza hypoxanthines were efficiently prepared from 6‐chloropurines/azapurines and DMSO under microwave irradiation. DMSO was employed as a readily available and atom‐economic methylthiomethylating reagent and solvent without any other activator. The mechanistic investigations demonstrate that the reaction proceeded via sequential SNAr reaction and the Pummerer rearrangement. The current protocol provides an effective strategy for the synthesis of various N1‐[(methylthio)methyl] (8‐aza)hypoxanthines.

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Section: Introductionmentioning

confidence: 99%

N¹‐Methylthiomethylation of (8‐Aza)6‐Chloropurine with DMSO through the Pummerer Rearrangement

Wang

Chen

2023

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Visible Light‐Mediated Late‐Stage Thioetherification of Mercaptopurine Derivatives

Ge,

Peng,

Xie

et al. 2024

Chemistry A European J

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We present herein a novel photo‐mediated homolytic C‐S bond formation for the preparation of alkylthiopurines and alkylthiopurine nucleosides. Despite the presence of reactive sites for the Minisci reaction, chemoselective S‐alkylation remained the predominant pathway. This method allows for the late‐stage introduction of a broad spectrum of alkyl groups onto the sulfur atom of unprotective mercaptopurine derivatives, encompassing 2‐, 6‐, and 8‐mercaptopurine rings. Organoborons serve as efficient and eco‐friendly alkylating reagents, providing advantages in terms of readily availability, stability, and reduced toxicity. Further derivatization of the thioetherified nucleosides, together with anti‐tumor assays, led to the discovery of potent anti‐tumor agents with an IC50 value reaching 6.1 µM (Comp. 31 for Jurkat).

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Palladium‐Catalyzed N³‐Directed C−H Halogenation of N⁹‐Arylpurines and Azapurines

Wang

et al. 2022

Eur J Org Chem

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A palladium‐catalyzed direct ortho‐halogenation of N9‐arylpurines was developed by using N‐halogenated succinimide (NBS/NCS/NIS) as the halogenation reagents. The current procedure offers a late‐stage strategy to generate N9‐(ortho‐haloaryl)purines in moderate to excellent yields. The protocol was applicable to the substrates with both electron‐rich and electron‐deficient substituents and only monohalogenated products were formed. Moreover, the purinyl N3‐atom was verified as the directing group to facilitate Pd‐catalyzed ortho‐C−H activation.

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Expedient synthesis of 2-alkylthio-N⁶-aryladenosines from guanosine

Cited by 4 publications

References 22 publications

N¹‐Methylthiomethylation of (8‐Aza)6‐Chloropurine with DMSO through the Pummerer Rearrangement

N¹‐Methylthiomethylation of (8‐Aza)6‐Chloropurine with DMSO through the Pummerer Rearrangement

Visible Light‐Mediated Late‐Stage Thioetherification of Mercaptopurine Derivatives

Palladium‐Catalyzed N³‐Directed C−H Halogenation of N⁹‐Arylpurines and Azapurines

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Expedient synthesis of 2-alkylthio-N6-aryladenosines from guanosine

Cited by 4 publications

References 22 publications

N1‐Methylthiomethylation of (8‐Aza)6‐Chloropurine with DMSO through the Pummerer Rearrangement

N1‐Methylthiomethylation of (8‐Aza)6‐Chloropurine with DMSO through the Pummerer Rearrangement

Visible Light‐Mediated Late‐Stage Thioetherification of Mercaptopurine Derivatives

Palladium‐Catalyzed N3‐Directed C−H Halogenation of N9‐Arylpurines and Azapurines

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Expedient synthesis of 2-alkylthio-N⁶-aryladenosines from guanosine

N¹‐Methylthiomethylation of (8‐Aza)6‐Chloropurine with DMSO through the Pummerer Rearrangement

N¹‐Methylthiomethylation of (8‐Aza)6‐Chloropurine with DMSO through the Pummerer Rearrangement

Palladium‐Catalyzed N³‐Directed C−H Halogenation of N⁹‐Arylpurines and Azapurines