52846-87-4

Upstream product

• 90-02-8 salicylaldehyde 
• 4392-24-9 Cinnamyl bromide 
• 2687-12-9 cinnamyl chloride 
• 637-50-3 1-phenylpropene 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 

Downstream Products

• 90404-55-0 3-Phenyl-2-p-tolyl-1,2,3,3a,4,9b-hexahydro-chromeno[4,3-c]pyrazole 
• 90404-57-2 2-(4-Chloro-phenyl)-3-phenyl-1,2,3,3a,4,9b-hexahydro-chromeno[4,3-c]pyrazole 
• 65487-87-8 2-(trans-2-phenylethenyl)benzo[b]furan 
• 77234-07-2 (2S,3R,3aS)-2,3-Diphenyl-2,3,3a,4-tetrahydro-chromeno[4,3-b]pyrrole 
• 77234-01-6 2,3-diphenylperhydropyrro<3,2-c>benzopyrane 
• 77234-06-1 (2S,3S,9bS)-2,3-Diphenyl-1,2,3,9b-tetrahydro-chromeno[4,3-b]pyrrole 
• 77234-02-7 cis-3-benzylamino-2-styryl-2,3-dihydrobenzofuran 
• 77234-02-7 trans-3-benzylamino-2-styryl-2,3-dihydrobenzofuran 
• 1338832-14-6 2-methoxy-14-phenyl-5,6,12,13-tetrahydro-5,12-dioxa-7-azadibenzo[a,h]anthracen-6-one 

Relevant academic research and scientific papers

Synthesis of benzofused cyclobutaoxepanones: Via intramolecular annulation of o -cinnamyl chalcones

Intramolecular stereoselective annulation of o-cinnamyloxy chalcones provides two kinds of tricyclic benzofused cyclobutaoxepanones via the synthesized routes of DABCO/NBS (1,4-diazabicyclo[2.2.2]octane/N-bromosuccinimide)-mediated Baylis-Hillman type cyc

Intramolecular [3+2]-cycloaddition of salicylaldehydes-based cyclic azomethine imines to access novel tetrahydrochromeno[4,3-c]pyrazolo[1,2-a]pyrazol-9-ones

An efficient intramolecular [3 + 2]-cycloaddition of in situ-formed salicylaldehyde-based N,N′-cyclic azomethine imines was successfully developed to access novel tetracyclic skeleton bearing three contiguous stereogenic centres. This established protocol features high functional-group tolerance, excellent chemical yields, good diastereoselectivities, and variable reaction conditions.

I2/DMSO-Promoted Synthesis of Chromeno[4,3- b ]quinolines through an Imine Formation/Aza-Diels-Alder/Aromatization Tandem Reaction under Metal-Catalyst- And Photosensitizer-Free Conditions

A tandem approach was developed for the efficient synthesis of substituted chromeno[4,3- b ]quinolines from arylamines and O -cinnamyl salicylaldehydes under metal-catalyst- and photosensitizer-free reaction conditions. Our protocol is based on an inexpensive I 2 /DMSO system in which molecular iodine first acts as a Lewis acid to promote the formation of the corresponding imine bearing the alkene moiety; then, this species fulfills a second role by catalyzing an intramolecular aza-Diels-Alder cycloaddition to generate the respective tetrahydrochromenoquinoline as an intermediate. Finally, the dual behavior of DMSO as an oxidant and as a solvent proved crucial at this stage, allowing the regeneration of I 2 and promoting the aromatization of the tetrahydrochromenoquinoline intermediates to yield the desired 7-aryl-6 H -chromeno[4,3- b ]quinolines. This protocol is mild and easy to perform, features high step-economy (tandem process) and provides a new access to biologically important nitrogen- and oxygen-containing heterocyclic molecules.

Asymmetric [2+2] photocycloadditionviacharge transfer complex for the synthesis of tricyclic chiral ethers

The asymmetric synthesis of chiral polycyclic ethers by an intramolecular [2+2] photocycloaddition is described. This process proceeded through a photocatalytically active iminium ion-based charge transfer (CT) complex under visible light irradiation. In this way a stereocontrolled [2+2] photocycloaddition is enabled leading to tricyclic products with good enantiomeric ratios.

Intramolecular Povarov Reactions for the Synthesis of Chromenopyridine Fused 2-Pyridone Polyheterocycles Binding to α-Synuclein and Amyloid-β Fibrils

A BF3·OEt2 catalyzed intramolecular Povarov reaction was used to synthesize 15 chromenopyridine fused thiazolino-2-pyridone peptidomimetics. The reaction works with several O-alkylated salicylaldehydes and amino functionalized thiazolino-2-pyridones, to generate polyheterocycles with diverse substitution. The synthesized compounds were screened for their ability to bind α-synuclein and amyloid β fibrils in vitro. Analogues substituted with a nitro group bind to mature amyloid fibrils, and the activity moreover depends on the positioning of this functional group.

Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis

This effort reports the first redox-neutral visible-light photocatalytic intramolecular dipolar cycloaddition for the diastereoselective synthesis of chromenoisoxazolidines. The authors have found that alkenylphenyl nitrones with a diverse substitution pattern on the aromatic ring and the alkenyl substituent undergo visible-light-promoted cycloadditions in the presence of catalytic amounts of Ru(bpy)3Cl2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.

Merging Visible-Light Photoredox and Lewis Acid Catalysis for the Intramolecular Aza-Diels–Alder Reaction: Synthesis of Substituted Chromeno[4,3-b]quinolines and [1,6]Naphthyridines

Substituted chromeno[4,3-b]quinolines and [1,6]naphthyridines were achieved by tandem intramolecular aza-Diels–Alder reaction using a strategy of combination of visible-light photoredox and Lewis-acid-catalysis. This intramolecular aza-Diels–Alder cycloaddition took place between the in situ generated benzylidene anilines derived from arylamines and salicylaldehyde or 2-aminoaryl aldehydes bearing a tethered alkene partner, followed by oxidative aromatization to give the target products. The study on the oxidative aromatization step revealed that it is much faster than the cyclization step; both the combination of imine and Lewis acid, and the combination of photocatalyst and Lewis acid under aerobic condition with the irradiation of visible light are efficient to achieve the transformation. This method provided a new access to the synthesis of important heterocycles under mild reaction conditions.

Silaborative Carbocyclizations of 1,7-Enynes. Diastereoselective Preparation of Chromane Derivatives

Palladium(0)-catalyzed carbocyclization of 1,7-enynes mediated by (chlorodimethylsilyl)pinacolborane proceeds with 1,8-addition of the silicon and boron functions to give functionalized cyclohexane derivatives with boron attached to the exocyclic olefin. A variety of chromane dervatives are accessible by this method. In contrast to the analogous reactions with 1,6-enynes, the configuration of the newly formed stereogenic center is controlled by a stereogenic center present in the substrate.

One-pot synthesis, biological evaluation, and docking study of new chromeno-annulated thiopyrano[2,3-c]pyrazoles

Abstract: A one-pot synthesis of new chromeno-annulated thiopyrano[2,3-c]pyrazoles has been achieved through a domino-Knoevenagel–hetero-Diels–Alder reaction after combining various pyrazol-5-thiones with O-alkenyloxy/alkynyloxy-salicylaldehydes/naphthaldehydes in a Br?nsted acidic ionic liquid, [Hmim]HSO4, methylimidazolium hydrogen sulphate, under microwave irradiation. The method is simple and in many cases the isolated products did not require further purification. The central pyranothiopyranyl cis-fusion was confirmed by 2D NMR NOESY and single-crystal X-ray analysis suggesting that the endo-E-Syn transition state would be the most favored pathway of the reaction. Many heterocycles of this new series were found active against six bacterial and two fungal strains. In addition, all the compounds possess good anti-oxidant activity with the ferric reducing anti-oxidant power value >100mmol/100g. All new structures were docked into active site of angiotensin I converting enzyme (ACE), assuming that the compounds possessed the anti-hypertensive activity potential on the basis of prediction of activity spectra of substances prediction results. Pyranyl ring oxygen in compound 9a forms two hydrogen bonds with HIS353 and HIS513 residues in the active site of the ACE having good G score (- 4.06) of this compound, comparable to that of the reference drug captopril (- 4.93). Graphical Abstract: [Figure not available: see fulltext.]

Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones

Allyl, dimethylallyl and prenyl ethers derived from o-acylphenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.