58134-00-2Relevant academic research and scientific papers
Efficient catalyst for tandem solvent free enantioselective Knoevenagel-formal [3+3] cycloaddition and Knoevenagel-hetero-Diels-Alder reactions
Fernandes, Sylvia,Rajakannu,Bhat, Sujata V.
, p. 67706 - 67711 (2015)
In this study a highly efficient catalyst has been observed for tandem solvent free enantioselective Knoevenagel-formal [3+3] cycloaddition and Knoevenagel-hetero-Diels-Alder reactions. Thus, the synthesis of bicyclic tetrahydro-2H-chromen-5(6H)-one and tricyclic octahydro-2H-benzo[c]-chromen-1(6H)-one derivatives with enantioselectivity up to ee 99% has been achieved in the presence of a chiral Lewis acid assisted Bronsted acid (LBA), titanium-isopropoxy-(S)-BINOLate under solvent free conditions. The stereochemistry of the tricyclic product 10 has been further supported by single crystal X-ray analysis. This domino powerful strategy combines both the economic and environmental aspects of organic chemistry, which are necessary for academic and industrial applications.
Thermal isomerization of cannabinoid analogues
Garcia, Angie,Borchardt, Dan,Chang, Chia-En A.,Marsella, Michael J.
, p. 16640 - 16641 (2009)
(Chemical Equation Presented) Thermal isomerization of CBCan to THCan [nonaromatic analogues of plant cannabinoids cannabichromene (CBC) and Δ1-tetrahydrocannabinol (THC), respectively] is predicted in silico and demonstrated experimentally. Density functional theory calculations support a similar isomerization mechanism for the corresponding plant cannabinoids. Docking studies suggest that THCan, although nonaromatic, has a CB1 receptor binding affinity similar to that of natural THC.
USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS
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Paragraph 0844; 0845, (2016/01/25)
The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.
Enantioselective wacker-type cyclization of 2-alkenyl-1,3-diketones promoted by Pd-SPRIX catalyst
Takenaka, Kazuhiro,Mohanta, Suman C.,Patil, Mahesh L.,Rao, C. V. Laxman,Takizawa, Shinobu,Suzuki, Takeyuki,Sasai, Hiroaki
supporting information; experimental part, p. 3480 - 3483 (2010/09/16)
(Equation Presented). An enantioselective intramolecular Wacker-type cyclization of 2-alkenyl-1,3-diketones catalyzed by a Pd(II)-SPRIX complex was developed. The reaction proceeded in a 6-endo-trig mode to give the desired chromene derivatives with moderate to good enantioselectivity. Isomerization of C-C double bonds via a π-allyl Pd intermediate was involved as the key step.
Environmentally benign, one-pot synthesis of pyrans by domino Knoevenagel/6π-electrocyclization in water and application to natural products
Jung, Ene Jin,Park, Byung Ho,Lee, Yong Rok
experimental part, p. 2003 - 2011 (2011/02/19)
In water medium, environmentally benign, facile, and efficient synthesis of pyrans was achieved in good yields by the reactions of a variety of cyclic 1,3-dicarbonyls with several α,β-unsaturated aldehydes. The key strategy was a formal [3+3] cycloaddition by domino Knoevenagel/6π- electrocyclization. This methodology was applied to the synthesis of biologically interesting pyranocoumarin, pyranoquinolinone, and pyranonaphthoquinone derivatives along with selected natural and non-natural products. The Royal Society of Chemistry 2010.
Metal-free Bronsted acid catalyzed formal [3 + 3] annulation. Straightforward synthesis of dihydro-2H-chromenones, pyranones, and tetrahydroquinolinones
Moreau, Julie,Hubert, Claudie,Batany, Jessika,Toupet, Loic,Roisnel, Thierry,Hurvois, Jean-Pierre,Renaudz, Jean-Luc
supporting information; experimental part, p. 8963 - 8973 (2010/03/04)
(Chemical Equation Presented) Bronsted acids catalyze the addition of enolizable β-diketones, β-ketoesters, and vinylogous amides to α,β-unsaturated aldehydes to lead to substituted chromenones, pyranones, and tetrahydroquinolinones in good yields under mild reaction conditions via a formal [3 + 3] cycloaddition.
Synthesis of spinochalcone B and analogues
Lee, Yong,Wang, Xue,Kim, Byung
, p. 2017 - 2025 (2007/10/03)
An efficient synthesis of spinochalcone B and its analogues is achieved from readily available 2H-pyran. Copyright Taylor & Francis Group, LLC.
A concise route for the synthesis of biologically interesting pyranocoumarins - Seselin, (±)-cis-khellactone, (±)- quianhucoumarin D, and the (±)-5-deoxyprotobruceol-I regioisomer
Lee, Yong Rok,Lee, Won Kyong,Noh, Seok Kyun,Lyoo, Won Seok
, p. 853 - 859 (2007/10/03)
An efficient synthesis of pyranocoumarins is achieved starting from 2H-pyrans. This process provides naturally occurring seselin, cis-khellactone, quianhucoumarin D, and the 5-deoxyprotobruceol-I regioisomer. Georg Thieme Verlag Stuttgart.
A Lewis acid-catalyzed formal [3 + 3] cycloaddition of α,β- unsaturated aldehydes with 4-hydroxy-2-pyrone, diketones, and vinylogous esters
Kurdyumov, Aleksey V.,Lin, Nan,Hsung, Richard P.,Gullickson, Glen C.,Cole, Kevin P.,Sydorenko, Nadiya,Swidorski, Jacob J.
, p. 191 - 193 (2007/10/03)
A Lewis acid-catalyzed formal cycloaddition of α,β-unsaturated aldehydes with 6-methyl-4-hydroxy-2-pyrone, 1,3-diketones, and vinylogous silyl esters is described here.
