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Usage

InChI:InChI=1/C11H8O4/c1-14-11(13)10-6-8(12)7-4-2-3-5-9(7)15-10/h2-6H,1H3

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 95-92-1 oxalic acid diethyl ester 
• 67-56-1 methanol 
• 4940-39-0 acide chromone carboxylique-2 
• 83-07-8 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one 
• 5112-47-0 4-oxo-4H-chromene-2-carbonyl chloride 
• 55386-79-3 1,3-dioxo-1-(2-hydroxyphenyl)butyl methyl ester 
• 553-90-2 Dimethyl oxalate 
• 622-29-7 N-Benzylidenemethylamine 
• 780-25-6 N-benzylidene benzylamine 
• 24431-15-0 N-benzyl-p-tolylmethanimine 

Downstream Products

• 36817-92-2 5-(2-hydroxy-phenyl)-1⁽²⁾H-pyrazole-3-carboxylic acid hydrazide 

Relevant academic research and scientific papers

SYNTHESIS OF SMALL MOLECULES INSPIRED BY PHOMOXANTHONE A

Methods, compositions, and kits are provided for synthesizing bioactive chromane, the method including: constructing a tertiary ether stereocenter enantioselectively by catalyzed alkynylation of a substituted chromenone to obtain a chromanone; reducing alkyne and ketone in the chromanone to obtain a chroman; and converting ester to methyl group thereby obtaining chromane.

Copper Bis(oxazoline)-Catalyzed Enantioselective Alkynylation of Benzopyrylium Ions

The stereocontrolled construction of biologically relevant chromanones and tetrahydroxanthones has been achieved through the addition of alkynes to benzopyrylium trilfates under the influence of copper bis(oxazoline) catalysis. Excellent levels of enantiocontrol (63–98 % ee) are achieved in the addition of a variety of alkynes to an array of chromenones with a hydrogen in the 2-position. Promising levels of enantiocontrol (54–67 % ee) are achieved in the alkynylation of chromenones with esters in the 2-position, generating tertiary ether stereocenters resembling those frequently found in naturally occurring metabolites.

Synthesis of functionalized chromones via organocatalysis

A facile and versatile organocatalytic approach to access 2-substituted and 2,3-disubstituted chromone derivatives under mild conditions was developed, which was effectively catalyzed by novel proline phenylsulphonylhydrazide or pyrrolidine. As a result, diversely functionalized chromones were obtained in up to 99% yield. In addition, further modification of the corresponding chromones afforded novel polycyclic chromones.

TMSI-Promoted vinylogous michael addition of siloxyfuran to 2-substituted chromones: A general approach for the total synthesis of chromanone lactone natural products

A concise and facile synthetic protocol for the construction of the 2-γ-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (±)-microdiplodiasone, (±)-lachnone C, and (±)-gonytolides C and G.

Synthesis and Structure-Activity Relationships of Triazaspirodecanone Derivatives as Nociceptin/Orphanin FQ Receptor Ligands

Several spiroxatrine derivatives were synthesized and evaluated as potential NOP receptor ligands. Structural modifications of the 1,4-benzodioxane moiety of spiroxatrine have been the focus of this research project. The structure-activity relationships that emerged indicate that the presence of an H-bond donor group (hydroxyl group) is more favorable for NOP activity when it is positioned α with respect to the CH2 linked to the 1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one portion. Moreover, cis diastereoisomers of the hydroxyl derivatives4 and 22 show a moderately higher degree of stereoselectivity than trans isomers. In particular, the spiropiperidine derivative cis-4 has submicromolar agonistic activity, and it will be the reference compound for the design and synthesis of new NOP agonists.

New tetracyclic 1,4-oxazepines constructed via practically simple tandem condensation strategy from readily available synthons

A streamlined synthetic methodology towards novel tetracyclic 1,4-oxazepines from readily available precursors is described. The compounds, designed as more soluble version of the earlier described, poorly soluble dibenzo[b,f][1,4]oxazepines, were obtained in high yields and as a single regioisomer as a result of three tandem chemical events - nucleophilic aromatic substitution, Smiles rearrangement and denitrocyclization.

Bioisosteric replacement and related analogs in the design, synthesis and evaluation of ligands for muscarinic acetylcholine receptors

Previous structure-activity relationship studies involving a series of lactone-based muscarinic ligands identified a lead compound containing a diphenylmethylpiperazine moiety (4; IC50 = 340 nM). The purpose of the present work is to investigate 1,3-benzodioxoles, 4,4-diethyl substituted tetrahydrofurans, 5-substituted oxazolidinones and chromones as bioisosteric replacements for the lactone ring in a novel series of muscarinic ligands. The approach provided compounds with improved % inhibition values and identified a non-selective muscarinic ligand with an IC50 value of 280 nM. The structure-activity relationship for this new series will be discussed. Selected compounds were evaluated in preliminary assays for subtype selectivity and were found to be non-selective.

Photocycloaddition reaction of methyl 2- and 3-chromonecarboxylates with various alkenes

The irradiation of methyl 2- and 3-chromonecarboxylate in the presence of various alkenes afforded cyclobutane type adducts, whose structures were established by X-ray structural analysis. Methyl 2-chromonecarboxylate showed higher photochemical reactivity than methyl 3-chromonecarboxylate, in which endo adducts were yielded as major products.

Exclusive photodimerization reactions of chromone-2-carboxylic esters depending on reaction media

The irradiation of chromone-2-carboxylic esters resulted in the stereo- and regioselective formation of C2 chiral anti-HH dimers from the triplet excited state. On the contrary, photolysis in the solid-state gave anti-HT dimers exclusively controlled by molecular arrangement in the crystal.

Synthesis of 2-alkyl-1-aryl-1,2-dihydrochromeno[2,3-c]pyrrole-3,9-dione derivatives

A preparative procedure for the synthesis of 2-alkyl-1-aryl-1,2- dihydrochromeno[2,3-c]pyrrole-3,9-diones from methyl 4-(o-hydroxyphenyl)-2,4- dioxobutanoate, aromatic aldehyde, and aliphatic amine is described.