N -9 Alkylation of purines via light-promoted and metal-free radical relay

Mao, Runze; Sun, Lifeng; Wang, Yong-Shi; Zhou, Min-Min; Xiong, De‐Cai; Li, Qin; Ye, Xin‐Shan

doi:10.1016/j.cclet.2017.08.005

Chinese Chemical Letters

2018

DOI: 10.1016/j.cclet.2017.08.005

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N -9 Alkylation of purines via light-promoted and metal-free radical relay

Runze Mao

Lifeng Sun

Yong-Shi Wang

et al.

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Cited by 8 publications

References 47 publications

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Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Grishin,

Mulina,

et al. 2024

Asian J Org Chem

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The use of C‐H compounds as reactive partners in a variety of transformations represents the state of the art in synthetic methodology. In this review, we have summarized the main achievements in using ethers as building blocks for the construction and modification of one of the basic platforms of organic chemistry, nitrogen‐containing heterocycles. Ethers, previously considered mainly as solvents, are excellent CH‐partners, capable of generating radical or cationic reactive species under the action of HAT agents and oxidants. The challenge in this field is the still limited number of heterocyclic systems and other starting reagents, with which the processes can be carried out selectively due to closer bond dissociation energies and oxidation potentials of heterocycles, reactive intermediates and ethers. However, the fine‐tuning of the reaction system using electro‐ and photochemical approaches and a deep understanding of the reaction pathways make the use of ethers as C‐H reagents a promising synthetic strategy.

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Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Grishin,

Mulina,

et al. 2024

Asian J Org Chem

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1,4‐Dioxane as Precursor of −CH₂CH₂−: A Simple and Convenient Strategy to Synthesize 1,2‐Disulfide Substituted Ethanes Initiated by Iodine

Liu,

Xie,

Wei

et al. 2024

Eur J Org Chem

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An unprecedented I2‐initiated nucleophilic ring opening reaction of 1,4‐dioxane with thiols for the construction of various 1,2‐disulfide substituted ethanes has been developed. Previously, dihalogenated ethane, acetylene or ethylene are often used as the pre‐cursor of ‐CH2CH2‐. Through the cleavage of two C–O bonds, 1,4‐dioxane as precursor of ‐CH2CH2‐ has been achieved for the first time. In the presence of HI, thiols could be replaced by disulfides as nucleophile. This protocol is very convenient and practical by its simple and mild conditions.

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Recent progress in the synthesis of N7(N9)-alkyl(aryl)purines (microreview)

Burcevs

Novosjolova²

2022

Chem Heterocycl Comp

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N -9 Alkylation of purines via light-promoted and metal-free radical relay

Cited by 8 publications

References 47 publications

Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

1,4‐Dioxane as Precursor of −CH₂CH₂−: A Simple and Convenient Strategy to Synthesize 1,2‐Disulfide Substituted Ethanes Initiated by Iodine

Recent progress in the synthesis of N7(N9)-alkyl(aryl)purines (microreview)

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Product

Resources

About

N -9 Alkylation of purines via light-promoted and metal-free radical relay

Cited by 8 publications

References 47 publications

Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

1,4‐Dioxane as Precursor of −CH2CH2−: A Simple and Convenient Strategy to Synthesize 1,2‐Disulfide Substituted Ethanes Initiated by Iodine

Recent progress in the synthesis of N7(N9)-alkyl(aryl)purines (microreview)

Contact Info

Product

Resources

About

1,4‐Dioxane as Precursor of −CH₂CH₂−: A Simple and Convenient Strategy to Synthesize 1,2‐Disulfide Substituted Ethanes Initiated by Iodine