68386-89-0Relevant academic research and scientific papers
Naphtho[2,3-: B] furan-4,9-dione synthesis via palladium-catalyzed reverse hydrogenolysis
Li, Jimei,Zhang, Jie,Li, Mingfei,Zhang, Chenyang,Yuan, Yongkun,Liu, Renhua
supporting information, p. 2348 - 2351 (2019/02/27)
A reverse hydrogenolysis process has been developed for two-site coupling of 2-hydroxy-1,4-naphthoquinones with olefins to produce naphtha[2,3-b]furan-4,9-diones and hydrogen (H2). The reaction is catalyzed by commercially available Pd/C without oxidants and hydrogen acceptors, thereby providing an intrinsically waste-free approach for the synthesis of functionalized and potentially biologically relevant naphtha[2,3-b]furan-4,9-diones.
Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids
Roman, Bart I.,De Ryck, Tine,Verhasselt, Sigrid,Bracke, Marc E.,Stevens, Christian V.
, p. 1027 - 1031 (2015/02/19)
In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.
Oxygen as single oxidant for two steps: Base-free one-pot Pd(ii)-catalyzed alcohol oxidation & arylation to halogen-intact β-aryl α,β-enones
Vellakkaran, Mari,Andappan, Murugaiah M. S.,Nagaiah, Kommu
, p. 45490 - 45494 (2014/12/10)
Using oxygen as the sole oxidant for two steps, we developed a new method to synthesize β-aryl α,β-enones by fine-tuning the Pd(ii)-catalyzed oxidation of allyl alcohol to subsequent arylation with arylboronic acids, arylboronic ester and aryltrifluoroborate salt. This one-pot green method does not require copper salt, base, and intermediate isolation. Halogen-bearing chalcones, dibenzylideneacetones and arylalkyl enones were synthesized in good yields. This journal is
Synthesis of 2-(1,5-diaryl-1,4-pentadien-3-ylidene)- hydrazinecarboximidamide hydrochloride catalyzed by p-dodecylbenzenesulfonic acid in aqueous media under ultrasound irradiation
Li, Ji-Tai,Du, Chao,Xu, Xiao-Ya,Chen, Guo-Fen
experimental part, p. 1033 - 1038 (2012/07/03)
Amidinohydrazone compounds are very important synthetic intermediates and can serve as versatile precursors in synthesis of many natural products and drug molecules. The use of ultrasound, p-dodecylbenzenesulfonic acid (DBSA) and water as solvent improved the synthesis of different 2-(1,5-diaryl-1,4- pentadien-3-ylidene)-hydrazinecarboximidamide hydrochlorides. The best reaction conditions for the condensation of 1,5-diphenyl-1,4-pentadien-3-one with aminoguanidine hydrochloride were as follows: 1,5-diphenyl-1,4-pentadiene-3-one (1, 1 mmol), aminoguanidine hydrochloride (1.1 mmol), DBSA (0.5 mmol), water 10 mL, reaction temperature 25-27°C, irradiation frequency 25 kHz. 2a was achieved in 94% yield within 2 h. The other seven amidinohydrazones were obtained in 84-94% yield within 2-3 h under the same conditions. Compared to the method involving catalysis by hydrochloric acid in refluxing EtOH, the advantages of present procedure are milder conditions, shorter reaction times, higher yields, and environmental friendly conditions, which make it a useful strategy for the synthesis of analogues.
Highly selective claisen-schmidt condensation catalyzed by silica chloride under solvent-free reaction conditions
Hazarkhani, Hassan,Kumar, Pradeep,Kondiram, Kadam Sachin,Shafi Gadwal, Ikhlas M.
experimental part, p. 2887 - 2896 (2010/10/20)
Silica chloride serves as a useful catalyst in the cross-aldol condensation, leading to the synthesis of a wide variety of bisarylidene cycloalkanones and chalcones. The catalyst showed high selectivity; self-condensation of ketones was not observed.
Tetrahydrothiapyran-4,ones - Source for annelated 1,2,3- selena/thiadiazoles and their reactivity
Bhaskar Reddy,Somasekhar Reddy,Subba Reddy
, p. 1342 - 1348 (2007/10/03)
1.2.3-Selenadiazole 4 and 1,2,3-thiadiazole 5 rings have been fused to 2.6-diaryl-(3-alkyl) tetrahydrothiapyran-4-ones 2 utilising α-ketomethylene group. The reactivity of the latter has also been studied viz., Beckmann rearrangement, Shapiro reaction. Strecker synthesis of α aminoacids etc.
CHLOROSULFONATION OF α,β-UNSATURATED ARYLIDENE KETONES
Cremlyn, Richard J.,Bassin, Jatinder P.,Graham, Steven,Saunders, David
, p. 135 - 142 (2007/10/02)
2-Thienylideneacetone (4), and the benzylidene derivatives of ethyl methyl ketone (19) and diethyl ketone (20) were reacted with excess chlorosulfonic acid to give the thienylidene 5,β-disulfonyl chloride (5) and the styrene disulfonyl chlorides (21 and 22).These were characterized by preparation of the sulfonamides (6-9, 23 and 24) required for screening as pest control agents.Benzylidene acetone (1) was condensed with aryl aldehydes to give the corresponding 1,5-diaryl-1,4-dien-3-ones (25-28), but the condensation failed with p-anisaldehyde and o-vanillin.Attempted chlorosulfonation of compounds (25 and 28) was unsuccessful and the products could not be characterised as sulfonamide derivatives.The 1H NMR spectra of selected compounds are briefly discussed.Key words: Chlorosulfonation of α,β-unsaturated arylidene ketones; thienylidene 5,β-disulfonyl chloride; styrene disulfonyl chlorides.
