Evidence map›Paper›PMID 34664211›Full record

ArticleArchives of pharmacal research2021

Site-selective and metal-free C-H nitration of biologically relevant N-heterocycles.

Junghyea Moon, Hyun Ku Ji, Nayoung Ko, Harin Oh, Min Seo Park, Suho Kim, Prithwish Ghosh, Neeraj Kumar Mishra, In Su Kim

Erratum issuedAbstract read
In one paragraph

Article in Archives of pharmacal research, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

2 citing papers in PubMed.

  1. Article
  2. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

9 authors.

Junghyea Moon *School of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
Hyun Ku JiSchool of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
Nayoung KoSchool of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
Harin OhSchool of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
Min Seo ParkSchool of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
Suho KimSchool of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea.
Prithwish GhoshSchool of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea.ORCID http://orcid.org/0000-0002-2731-8575
Neeraj Kumar MishraSchool of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea. neerajchemistry@gmail.com.ORCID http://orcid.org/0000-0001-9955-7535
In Su KimSchool of Pharmacy, Sungkyunkwan University, Suwon, 16419, Republic of Korea. insukim@skku.edu.ORCID http://orcid.org/0000-0002-2665-9431

Funding

National Research Foundation of Korea 2019R1A4A2001451National Research Foundation of Korea 2020R1A2C3005357
6 · The paper itself

Abstract

The site-selective and metal-free C-H nitration reaction of quinoxalinones and pyrazinones as biologically important N-heterocycles with t-butyl nitrite is described. A wide range of quinoxalinones were efficiently applied in this transformation, providing C7-nitrated quinoxalinones without undergoing C3-nitration. From the view of mechanistic point, the radical addition reaction exclusively occurred at the electron-rich aromatic region beyond electron-deficient N-heterocycle ring. This is a first report on the C7-H functionalization of quinoxalinones under metal-free conditions. In contrast, the nitration reaction readily takes place at the C3-position of pyrazinones. This transformation is characterized by the scale-up compatibility, mild reaction conditions, and excellent functional group tolerance. The applicability of the developed method is showcased by the selective reduction of NO

Indexed as

Aniline CompoundsChemistry Techniques, SyntheticNitritesPyrazinesQuinoxalinesAniline Compoundsn-butyl nitriteNitritesPyrazinesQuinoxalinesC–H functionalizationHeterocyclesNitrationRegioselectivityt-Butyl nitrite

Identifiers

PMID34664211
PMCPMC8685193

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.