28809-06-5

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 4392-24-9 Cinnamyl bromide 
• 28752-82-1 2-(allyloxy)benzaldehyde 
• 90-01-7 salicylic alcohol 
• 106-95-6 allyl bromide 

Downstream Products

• 28809-12-3 1-methyl-3c-phenyl-(3ar,9bc)-1,3a,4,9b-tetrahydro-3H-chromeno[4,3-c]isoxazole 
• 135192-09-5 2-(ethylimino)-4-phenyl-1,2,3,4,4a,10b-hexahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine 
• 127056-11-5 N,N-Dimethyl-N'-[(E)-3-[2-((E)-3-phenyl-allyloxy)-phenyl]-prop-2-en-(E)-ylidene]-hydrazine 
• 135192-08-4 2-<(4-chlorophenyl)imino>-4-phenyl-1,2,3,4,4a,10b-hexahydro-5H-<1>benzopyrano<4,3-d><1,3>thiazine 
• 91153-89-8 C₂₂H₁₉NO₂ 
• 65487-87-8 2-(trans-2-phenylethenyl)benzo[b]furan 
• 60206-81-7 cis-3,4-dihydro-3-(phenylmethyl)-2H-1-benzopyran-4-ol 
• 60206-81-7 (+/-)-(3R,4S)-3-benzylchroman-4-ol 
• 89-95-2 2-methyl-benzyl alcohol 

Relevant academic research and scientific papers

Straightforward synthesis and biological evaluation as topoisomerase I inhibitors and antiproliferative agents of hybrid Chromeno[4,3-b][1,5]Naphthyridines and Chromeno[4,3-b][1,5]Naphthyridin-6-ones

This work describes the synthesis of hybrid tetrahydro-1,5-naphthyridine and 1,5-naphthyridine derivatives fused with heterocycles such as chromenes and chromen-2-ones or coumarins, which were synthesized in good to high general yields. The synthetic rout

The First Domino Reduction/Imine Formation/Intramolecular Aza-Diels–Alder Reaction for the Diastereoselective Preparation of Tetrahydrochromano[4,3-b]quinolines

The first domino reduction/imine formation/intramolecular aza-Diels–Alder reaction is reported. Tetrahydrochromano[4,3-b]quinolines are formed with high exo-E-anti selectivity and yields up to 87 % when a nitrobenzene and a 2-(cinnamyloxy)benzaldehyde are reacted in aqueous citric acid by using iron as a reductant and montmorillonite K10 as a catalyst. The domino process starts with the in situ reduction of the nitrobenzene to the corresponding aniline, which is followed by imine formation and terminated by an intramolecular aza-Diels–Alder reaction.

Palladium-catalyzed intramolecular carboesterification of olefins

One catalyst three bonds: The title reaction between propiolic acids and unactivated olefins (see scheme; O red, Cl green) results in vicinal functionalization of the olefin, with the formation of new C-C and C-O bonds. Structurally complex 6,7,5-tricyclic ring systems are formed in a single step by this cascade chloropalladation and formal [3+2] cycloaddition.

Microwave-assisted solvent-free intramolecular 1,3-dipolar cycloaddition reactions leading to hexahydrochromeno[4,3-b]pyrroles: scope and limitations

We report the microwave-assisted solvent-free synthesis of hexahydrochromeno[4,3-b]pyrroles. Intramolecular 1,3-dipolar cycloadditions proceed under these conditions within 15-40 min in 16-84% yields. An influence of the microwave irradiation upon various [3+2] cycloaddition reaction intermediates was studied. Additionally, a scope and limitations of these reactions including an influence of the dipolarophile geometry upon the cycloaddition selectivity and steric demands of the dipole upon its reactivity were also disclosed. These observations led us to postulate a preferable transition state of the reaction. Finally, an influence of the microwave irradiation to the isomerization of activated olefins was also described.

Cascade reactions: Sequential homobimetallic catalysis leading to benzofurans and β,γ-unsaturated esters

The concatenation between a Pd(0)-promoted deallylation catalytic cycle and a Pd(II)-promoted heterocyclization catalytic cycle (an example of what we have named "sequential homobimetallic catalysis") has been shown to occur starting from 1-(2-allyloxyphenyl)-2-yn-1-ols 1 to afford 2-benzofuran-2- ylacetic esters 2 and β,γ-unsaturated esters in high yields under carbonylative conditions. In view of the conceptual as well as the synthetic importance of the process, the mechanistic aspects and the synthetic scope of the reaction have been investigated in detail. All the experimental evidence is in agreement with the sequential homobimetallic mechanism, and the reaction has proven to be of general synthetic applicability.

Microwave-Assisted [3 + 2] Cycloadditions of Azomethine Ylides

(Equation Presented) The microwave-assisted intramolecular [3 + 2] cycloaddition reaction of azomethine ylides to activated and nonactivated alkenes and alkynes is described. The procedure allows the synthesis of pyrrolidines and pyrrole products in good to excellent overall yields in short reaction times. It appears from parallel comparative studies that the microwave procedure favors the reaction times and overall purity of the crude reaction mixture. The reactions can also be performed in the absence of solvent.

Regioselectivity in the intramolecular allyl transfer reaction catalysed by electrogenerated nickel complexes: Influence of metal ions

The intramolecular transfer of allyl moieties from substituted allyl aryl ethers to carbonyl groups has been studied by electrosynthesis, in a nickel-catalysed reaction. The influence of metal ions such as Mg2+, Zn2+ and Al3+ has been examined. Regioselectivity towards the branched isomer was better with Zn2+ than with Mg2+ ions, but it was higher in the absence of added metal ions.

Palladium-catalyzed allylating heteroannulation of o-alkynyl-allyloxybenzenes. A route to 2-substituted-3-allylbenzo[b]furans

In the presence of palladium(0), o-alkynyl allyloxybenzenes produce 2-substituted 3-allylbenzo[b]furans in fair yields. This heteroannulation is promoted by the η3-allyl palladium species issued from early reaction of the catalyst with the starting allyl aryl ether.