Skeletal Editing Via CH→N Atom Swapping in Fused Imidazoles: Access to Triazolo[5,1- <i>a</i> ]isoquinoline, Triazolo[1,5- <i>a</i> ]quinoline, and Triazolo-[1,5- <i>a</i> ]pyridines Frameworks

Herein, we report a practical and efficient carbon-to-nitrogen atom swap in 2-phenylimidazo[2,1-<i>a</i>]isoquinoline and 2-phenylimidazo[1,2-<i>a</i>]quinoline scaffolds, enabling their direct conversion to the corresponding 2-phenyl-[1,2,4]triazolo[5,1-<i>a</i>]isoquinoline and 2-phenyl-[1,2,4]triazolo[1,5-<i>a</i>]quinoline analogues. This transformation exploits the intrinsic reactivity of the parent heterocycles to undergo a cascade sequence involving oxidative cleavage, amination, and cyclization (OCAC) under mild conditions with functional group tolerance.

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Publication Details

Journal
Organic Letters
Published
2025-10-14
DOI
https://doi.org/10.1021/acs.orglett.5c03592
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Skeletal Editing Via CH→N Atom Swapping in Fused Imidazoles: Access to Triazolo[5,1- a ]isoquinoline, Triazolo[1,5- a ]quinoline, and Triazolo-[1,5- a ]pyridines Frameworks

Bhupesh Sharma, Ravi Shankar, Yashika Sharma, Younis Rasool
Organic Letters
Catalytic C–H Functionalization Methods
article

Skeletal Editing Via CH→N Atom Swapping in Fused Imidazoles: Access to Triazolo[5,1- a ]isoquinoline, Triazolo[1,5- a ]quinoline, and Triazolo-[1,5- a ]pyridines Frameworks

Bhupesh Sharma, Ravi Shankar, Yashika Sharma, Younis Rasool
article en

Abstract

Herein, we report a practical and efficient carbon-to-nitrogen atom swap in 2-phenylimidazo[2,1-<i>a</i>]isoquinoline and 2-phenylimidazo[1,2-<i>a</i>]quinoline scaffolds, enabling their direct conversion to the corresponding 2-phenyl-[1,2,4]triazolo[5,1-<i>a</i>]isoquinoline and 2-phenyl-[1,2,4]triazolo[1,5-<i>a</i>]quinoline analogues. This transformation exploits the intrinsic reactivity of the parent heterocycles to undergo a cascade sequence involving oxidative cleavage, amination, and cyclization (OCAC) under mild conditions with functional group tolerance.

Organic LettersVol. 27(42)
Indian Institute of Integrative Medicine (IN), Applied Natural Sciences (US), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 78%
Catalytic C–H Functionalization Methods
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