16336-27-9

Usage

Also known as

6-chloro-4H-chromen-2-one

Classification

Chromene derivative

Structure

Heterocyclic compound with a chlorine atom attached to the 6th carbon of the chromene ring

Pharmaceutical applications

Studied for its anticancer and antiviral properties

Use

Building block in the synthesis of other biologically active compounds

Properties

Aromatic and heterocyclic

Application

Useful in medicinal chemistry and drug discovery

Upstream product

• 19130-39-3 1-chloro-4-(prop-2-yn-1-yloxy)benzene 
• 90448-23-0 4-Chloro-1-(3-chloro-2-propenoxy)benzene 
• 33533-99-2 6-chloro-4H-chromen-4-one 
• 1826-67-1 vinyl magnesium bromide 
• 635-93-8 5-chlorosalicyclaldehyde 
• 106-48-9 4-chloro-phenol 
• 108-24-7 acetic anhydride 
• 122323-08-4 3-Bromo-6-chloro-2H-chromene 

Relevant academic research and scientific papers

RADICAL CYCLISTION: SYNTHESIS OF 4H-FURO(3,2-c)-1-BENZOPYRANS

3,4-dihydro-3-bromo-4-(prop-2-ynyloxy)-2H-1-benzopyrans (3) undergo radical cyclisation when treated with nBu3SnH and AlBN to give good yield of 2,3,3a,9b,-tetrahydro-3-methylene-4H-furo(3,3-c)benzopyran (4).

Synthesis of 2H-chromenes through the reduction of chromones with 9-BBN

Chromones were regioselectively reduced to 2H-1-benzopyrans through the 1,2-addition of 9-borabicyclo-[3.3.1]nonane. Although transition-metal complexes did not have a catalytic effect on the reaction, only by using palladium(II) chloride, could both 2H-1-benzopyran and dihydro-1-benzopyran be obtained to a similar extent. Also, the reduction of chromone using other organoboranes led not to 2H-1-benzopyran, but rather to chromanone through the reduction of only an olefin moiety.

A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes

The gold(i)-catalyzed endo-cyclization of o-(1-hydroxyallyl)phenols to form chromenes is reported. The title compounds are prepared in high yield from readily available substrates. The system tolerates both electron rich and deficient aryl rings and a high degree of substitution on the allyl moiety.

A New Route to o-Allenylphenols

Cathodic reduction of 3-bromochromenes led to a ring-opening reaction yielding o-allenylphenyl acetates.

Novel electrochemical route to 2-(α-alkoxyallyl)phenols - Cathodic eliminative ring opening reaction

Electrochemical reduction of 4-alkoxy-3-bromochromans in acetonitrile led to a facile ring cleavage reaction yielding (2(α-alkoxy- allyl)phenols which are not easily accessible.

Radical cyclisation of 4-(o-Bromophenoxy)-2H-1-benzopyrans; an Efficient Synthesis of Pterocarpans

The preparation of 4-(o-bromophenoxy)-2H-1-benzopyrans and their conversion into the pterocarpan skeleton via radical cyclisation are reported.

THERMAL REARRANGEMENT OF THE γ-CHLOROALLYL ETHERS OF PHENOLS. THE FORMATION OF 2H-CHROMENES

The termal rearrangement of the γ-chloroallyl ethers of phenols takes place as an intramolecular -sigmatropic Claisen rearrangement.The final compounds are not the Claisen phenols but the products from their subsequent transformations, i.e., 2H-chrom

CLAISEN REARRANGEMENT OF ARYL PROPARGYL ETHERS IN POLY(ETHYLENE GLYCOL) - A REMARKABLE SUBSTITUENT AND SOLVENT EFFECT

The Claisen rearrangement of aryl propargyl ethers in poly(ethylene glycol)-200 at 220 o C affords products in good yields.Aryl propargyl ethers containing electron donating groups yield (2H)-benzopyrans and those containing electron withdrawing groups yield 2-methylbenzofurans.