Synthesis of 3-Hydroxy-4-Substituted Picolinonitriles from 4-Propargylaminoisoxazoles via Stepwise and One-Pot Isoxazolopyridine Formation/N–O Bond Cleavage Sequence

Fukuhara, Shintaro; Yugandar, Somaraju; Fuse, Shinichiro; Nakamura, Hiroyuki

doi:10.1021/acsomega.8b03114

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2019

2023

Publication Types

Select...

Article4

Book1

Relationship

Self Cite2

Independent3

Authors

Journals

Cited by 6 publications

(1 citation statement)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Isoxazoles, the five-membered heteroaromatic compounds containing an N–O bond in the ring, are widely used as a useful building block in the synthesis of complex natural products and multifunctionalized molecules . Conventional synthetic approaches of functionalized isoxazoles are based on ring construction with prefunctionalized linear components .…”

mentioning

confidence: 99%

Photochemical Conversion of Isoxazoles to 5-Hydroxyimidazolines

2020

Self Cite

View full text Add to dashboard Cite

Photochemical conversion of isoxazole I to 5-hydroxyimidazoline VII proceeded via the trapping of the photogenerated acylazirine III with amines under UV light irradiation. This is the first report of the efficient synthesis of 5-hydroxyimidazolines that are not readily accessible by other means. 5-Hydroxyimidazolines were also converted into multisubstituted imidazoles in one step by treatment with trifluoroacetic anhydride (TFAA) and 2,6-lutidine in dichloromethane.

show abstract

mentioning

confidence: 99%

Photochemical Conversion of Isoxazoles to 5-Hydroxyimidazolines

2020

Self Cite

View full text Add to dashboard Cite

show abstract

Methylene Insertion into Nitrogen‐Heteroatom Single Bonds of 1,2‐Azoles via a Zinc Carbenoid: An Alternative Tool for Skeletal Editing

Tsuda,

Morita,

Morita

et al. 2023

Advanced Science

Self Cite

View full text Add to dashboard Cite

The nitrogen‐heteroatom single bonds of 1,2‐azoles and isoxazolines underwent methylene insertion in the presence of CH2I2 (6 equiv.) and diethylzinc (3 equiv.) to produce a wide variety of the ring‐expanded six‐membered heterocycles. Density functional theory calculations suggest that the methylene insertion proceeds via cleavage of nitrogen‐heteroatom single bonds followed by ring closure.

show abstract