Facile synthesis of isoquinolines and isoquinoline<i>N</i>-oxides<i>via</i>a copper-catalyzed intramolecular cyclization in water

Zhang, Lujun; Xiong, Wenfang; Yao, Biao; Liu, Haitao; Li, Meng; Qin, Yu; Yu, Yujian; Li, Xu; Chen, Meng; Wu, Wanqing; Li, Jianxiao; Wang, Jinliang; Jiang, Huanfeng

doi:10.1039/d2ra06097c

Cited by 8 publications

(6 citation statements)

References 69 publications

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“…The o-alkynyl benzaldehyde oximes 1a−g were prepared by already described protocols. 24 The and arylseleninic acids 2a−g were previously prepared as described in the Supporting Information. 25 General Procedure for the Synthesis of 3-Organyl-4-(selanyl)isoquinoline-2-oxides (3a−3s).…”

Section: Discussionmentioning

confidence: 99%

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Anghinoni,

Ferreira,

Kazmierczak

et al. 2024

J. Org. Chem.

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Herein, we describe the use of benzeneseleninic acid derivatives (BSA) as a bench-stable and easy to handle selenium reagent to access 4-(selanyl)isoquinoline-N-oxides through the selenocyclization of o-alkynyl benzaldehyde oximes. The reaction is conducted in refluxing methanol, allowing the thermal generation of electrophilic selenium species in situ. By this new protocol, a library of 19 selenium-decorated N-oxide isoquinolines was accessed in up to 96% yield with an outstanding substrate tolerance and the feasibility to scale it up 10 times (from 0.25 to 2.5 mmol).

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Section: Discussionmentioning

confidence: 99%

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Anghinoni,

Ferreira,

Kazmierczak

et al. 2024

J. Org. Chem.

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“…The synthesis of isoquinolines and isoquinoline N -oxides via a Cu(I)-catalyzed intramolecular cyclization of ( E )-2-alkynylaryl oxime derivatives was disclosed by Li and Jiang et al in 2022 (Scheme ). The selective N–O/O–H cleavage could be triggered by switching on/off a hydroxyl protecting group of oximes, providing a series of isoquinolines and isoquinoline N -oxides, respectively. In the presence of 10 mol % CuI as the catalyst, H 2 O (2 mL) as the green and safe solvent, and ligand and additive free conditions, this protocol provided an efficient and eco-friendly way for the assembly of structurally diverse isoquinolines and isoquinoline N -oxides in moderate to good yields with good functional group tolerance.…”

Section: Synthesis Of Nitrogen-containing Heterocyclementioning

confidence: 99%

Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect

Zheng,

Li,

et al. 2024

Org. Process Res. Dev.

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Oxygen-, nitrogen-, and sulfur-containing heterocycles exhibit remarkable biological and pharmaceutical activities that are often found in naturally occurring products, pharmaceutical molecules, and synthetic compounds. Therefore, the synthesis of heterocycle building blocks has gained huge attention in the past decade. Compared with the modification of heterocyclic compounds, the construction of heterocyclic compounds from scratch is more attractive. In this Perspective, we describe our recent advances in the rational design and strategic application of the de novo synthesis of various synthetically and biologically important heterocycles. The organization of the Perspective is categorized in the following order: (a) type of heterocycle, (b) ring size of heterocycle, (c) number of heteroatoms, and (d) fused heterocycles. Moreover, some significant and representative synthetic methodologies and their synthetic applications and brief reaction mechanisms have also been described. We hope that this Perspective will help to provide a guideline for researchers who are interested in this fertile area.

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“…Zhang et al developed a selective synthetic protocol for furnishing isoquinolines 320 and isoquinoline N -oxides 321 (Scheme 66). 111 Copper catalysed intramolecular cyclization of alkynyl aryl imine 318 generates the isoquinoline intermediate 319 . The various adducts of compounds 319a–b under thermal conditions afford isoquinolines 320 and 321 , respectively.…”

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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Facile synthesis of isoquinolines and isoquinolineN-oxidesviaa copper-catalyzed intramolecular cyclization in water

Abstract: A facile copper-catalyzed intramolecular cyclization for the selective synthesis of isoquinolines and isoquinoline N-oxides in water is described.

Cited by 8 publications

References 69 publications

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Synthesis of Selenium-Decorated N-Oxide Isoquinolines: Arylseleninic Acids in Selenocyclization Reactions

Oxygen-, Nitrogen-, and Sulfur-Containing Heterocycles: Recent Advances in De Novo Synthesis and Prospect

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

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