6190-73-4

Upstream product

• 1322774-99-1 2-(3-cyclohexylpropynoyl)phenol 
• 1322775-85-8 1-(o-hydroxyphenyl)-3-cyclohexylpropargylic alcohol 
• 931-48-6 2-cyclohexylacetylene 
• 90-02-8 salicylaldehyde 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 1403475-67-1 2-(3-cyclohexylpropioloyl)phenylacetate 
• 118-93-4 o-hydroxyacetophenone 
• 3289-28-9 ethyl cyclohexanecarboxylate 
• 1198006-64-2 C₁₅H₁₈O₃ 
• 491-38-3 1-benzopyran-4(4H)-one 
• 110-82-7 cyclohexane 
• 533-58-4 2-Iodophenol 
• 201230-82-2 carbon monoxide 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 

Relevant academic research and scientific papers

Visible Light-Induced Regioselective Decarboxylative Alkylation of the C(sp2)?H Bonds of Non-Aromatic Heterocycles

With sunlight or blue LEDs irradiation, regioselective decarboxylative alkylation of various non-aromatic heterocycles has been realized via C(sp3)-centered radical C(sp2)?C(sp3) bond formation under oxidant-free condition

Nickel catalysed carbonylative Sonogashira reaction for the synthesis of diarylalkynones and 2-substituted flavones

The nickel catalyzed, palladium/phosphine free carbonylative Sonogashira reaction of terminal alkynes with substituted aryl and heteroaryl iodides is described. This protocol provides mild and robust conditions to synthesize a variety of substituted aryl α,β-alkynyl ketones and flavones in good to excellent isolated yields. This methodology tolerates several functional groups such as electron donating (methyl, isopropyl, tert-butyl, methoxy) as well as electron withdrawing (trifluoromethyl, nitro, esters, nitrile) groups on the terminal alkynes and iodides.

L-ascorbic acid: A green and competent promoter for solvent-free synthesis of flavones and coumarins under conventional as well as microwave heating

Background: An expeditious approach has been developed for the synthesis of two distinct classes of benzopyrones viz. flavones and coumarins under solvent-free conditions. L-Ascorbic acid was found to be an effective promoter under microwave irradiation and conventional heating. Various benzo-α-pyrones and benzo-γ-pyrones were synthesized with overall good yields. The present protocol is highly facile and needs no column chromatography for purification and therefore it would serve as an effective and compatible method under both microwave irradiation and conventional heating. Results: The catalytic ability of L-ascorbic acid was investigated for the synthesis of flavones and coumarins. For this purpose, cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanedione and Pechmann coumarin synthesis, reactions were selected. And accordingly, it was observed that one mole of L-ascorbic acid was necessary for the completion of reaction. In all the cases, the desired flavones were smoothly generated with good to excellent yields; indicating its excellent tolerance for various functional groups. However, electron donating groups favors coumarin synthesis under these conditions. All the reaction mixtures were carefully analyzed and NMR indicates high conversions and lack of side products. Conclusion: We have developed L-ascorbic acid-promoted, solvent-free and simple method for the synthesis of benzo-α-pyrones and benzo-γ-pyrone under microwave irradiation as well as conventional heating in good to excellent yields. The notable advantages of this method are solvent-free conditions, inexpensive and efficient eco-friendly promoter, and shorter reaction time and can be carried out under air. This methodology is highly facile and requires no column chromatography for purification. The resulting flavones and coumarins are versatile building blocks in the construction of heterocyclic architectures, dominant in natural products. Further studies of exploiting the efficiency of L-ascorbic acid as a promoter in synthesis of various heterocyclic compounds are in progress.

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.

Ammonium acetate promoted rapid and efficient synthesis of γ-Benzopyranones and 3,4-dihydropyrimidin-2(1H)-ones/thiones under solventfree conditions: A parallel scrutiny of microwave irradiation versus conventional heating

Simple and highly efficient approach for the synthesis of γ-Benzopyranones and 3,4-Dihydropyrimidin-2(1H)-ones/thiones using ammonium acetate as a promoter under thermal as well as microwave irradiation using solvent-free conditions has been demonstrated.

An efficient and green synthesis of flavones using natural organic acids as promoter under solvent-free condition

An efficient and eco-friendly synthesis of flavones, promoted by naturally occurring acids, via cyclodehydration of 1-(2-hydroxyphenyl)-3-aryl-1,3- propanediones using conventional and microwave heating under solvent-free condition is described.

Hypervalent iodine-mediated selective oxidative functionalization of (thio)chromones with alkanes

C-C bond formation is the most fundamental way for the chain propagation in organic molecules. This achievement through tandem oxidation of two different C-H bonds represents the state of the art in organic synthesis. Selective functionalization of the ubiquitous aliphatic C-H bonds offers an attractive option for this oxidative cross-coupling methodology. To develop such a methodology under mild and metal-free conditions remains challenging. Herein, we report hypervalent iodine-mediated selective oxidative functionalization of aliphatic C-H bonds of alkanes with chromones and (thio)chromones. A wide range of alkanes, both cyclic and acyclic, has been found to react selectively and predictably in good yields. The developed methodology is also the first report of a direct oxidative functionalization of the C-2 position of (thio)chromones with alkanes to access bioactive compounds. Hypervalent iodine: An efficient IIII-mediated selective oxidative functionalization of alkanes with chromones and (thio)chromones has been developed. The developed methodology provides a direct access to the 2-alkyl chromones under metal-free and ambient conditions. Both cyclic and acyclic alkanes can be selectively functionalized (see scheme).

Ruthenium-NHC-catalyzed asymmetric hydrogenation of flavones and chromones: General access to enantiomerically enriched flavanones, flavanols, chromanones, and chromanols

Two to four! Readily available flavones and chromones were efficiently converted into four valuable chiral classes of O-heterocycles - flavanones, chromanones, flavanols, and chromanols - by means of an enantioselective Ru/NHC-catalyzed hydrogenation process (see scheme; NHC=N-heterocyclic carbene, PCC=pyridinium chlorochromate). Copyright

Synthesis of flavones and γ-benzopyranones using mild sonogashira coupling and 18-crown-6 ether mediated 6-endo cyclization

An efficient method for the synthesis of flavones and γ- benzopyranones has been developed utilizing a mild Sonogashira coupling and 18-crown-6 ether mediated 6-endo cyclization of o-alkynoylphenyl acetates. By using this strategy, flavones and γ-benzopyranones bearing electron-donating groups, halogens, and simple alkyl substituents were synthesized in satisfactory yields. A facile, mild, and selective method for the synthesis of flavones and γ-benzopyranones is reported. o-Alkynoylphenyl acetates were obtained from either acyl chloride derivatives or substituted salicylates. Upon removing the acetate group, flavones and γ- benzopyranones were synthesized within 15 min with the aid of 18-crown-6 ether. A library of flavones and γ-benzopyranones was established. Copyright