C–H/N–H Annulation of <i>N</i> -Aryl Triazolinediones with Diazo Compounds: A Route to Cinnoline Analogues

The preparation and functionalization of cinnolinones and dihydrocinnolinones have emerged as important topics in medicinal chemistry and drug discovery. In this study, we report an iridium(III)-catalyzed C-H/N-H annulation between <i>N</i>-aryl triazolinediones and diazo Meldrum's acid to access a range of dihydrocinnolinones. Furthermore, by modulation of the reaction conditions, a ruthenium(II)-catalyzed annulative cyclization of <i>N</i>-aryl triazolinediones with α-diazo-β-ketoesters was developed to efficiently produce cinnolines.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-05
DOI
https://doi.org/10.1021/acs.joc.5c02497
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

C–H/N–H Annulation of N -Aryl Triazolinediones with Diazo Compounds: A Route to Cinnoline Analogues

Jungmin Kang, Amitava Rakshit, Taejoo Jeong, Jung‐Hwan Choi et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

C–H/N–H Annulation of N -Aryl Triazolinediones with Diazo Compounds: A Route to Cinnoline Analogues

Jungmin Kang, Amitava Rakshit, Taejoo Jeong, Jung‐Hwan Choi, Jeeyeon Kim, In Su Kim, Pargat Singh, Seongwon Hong, Seohyeon Jang, Jin Ho Jeong
article en

Abstract

The preparation and functionalization of cinnolinones and dihydrocinnolinones have emerged as important topics in medicinal chemistry and drug discovery. In this study, we report an iridium(III)-catalyzed C-H/N-H annulation between <i>N</i>-aryl triazolinediones and diazo Meldrum's acid to access a range of dihydrocinnolinones. Furthermore, by modulation of the reaction conditions, a ruthenium(II)-catalyzed annulative cyclization of <i>N</i>-aryl triazolinediones with α-diazo-β-ketoesters was developed to efficiently produce cinnolines.

The Journal of Organic ChemistryVol. 90(50)
Bioscience Research (US), Hanmi Pharmaceutical (South Korea) (KR), Sungkyunkwan University (KR)
Openalex Percentile: Top 71%
Catalytic C–H Functionalization Methods
DOISourceOpenAlex
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C–H/N–H Annulation of <i>N</i> -Aryl Triazolinediones with Diazo Compounds: A Route to Cinnoline Analogues — Jungmin Kang, Amitava Rakshit, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS