40105-30-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 536, 1986 DOI: 10.1021/jo00354a026

InChI:InChI=1/C11H9NO/c1-8-6-9(7-13)12-11-5-3-2-4-10(8)11/h2-7H,1H3

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 67-56-1 methanol 
• 1198-37-4 2,4-dimethylquinoline 
• 33787-85-8 (4-methyl-quinolin-2-yl)-methanol 
• 99687-44-2 2-(dioxolan-2-yl)-4-methylquinoline 
• 40105-26-8 4-methyl-2-(1,3,5-trioxan-2-yl)quinoline 
• 20461-86-3 2,2-diethoxy acetic acid 
• 2566-44-1 1-cyclopropylethanol 
• 607-66-9 4-methylquinolin-2-ol 
• 64658-04-4 2-bromo-4-methyl-quinoline 
• 68-12-2 N,N-dimethyl-formamide 
• 201230-82-2 carbon monoxide 
• 7446-08-4 selenium(IV) oxide 

Relevant academic research and scientific papers

Redox-triggered interconversion between piperidine chair conformations in a Cu(I/II) complex

A redox-induced six-membered ring chair-chair conformational interconversion in a copper-coordinated trans-piperidine tripodal ligand is demonstrated. Each group of the 1,2,3-substituted ring can potentially ligate the metal; two equatorial groups ligate the metal in the CuI state leaving a disassociated, axial group. However, all three groups (two axial and one equatorial) ligate the metal in the CuII state. Exciton-coupled circular dichroism (ECCD) and 2D NMR were used to characterize the structures.

Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines

The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.

Methanol as a formylating agent in nitrogen heterocycles

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Photoredox-Catalyzed Redox-Neutral Minisci C?H Formylation of N-Heteroarenes

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Synthesis and anti-norovirus activity of pyranobenzopyrone compounds

During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 μM and TD50 values of >200 and 96.4 μM, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents.

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