5706-14-9Relevant academic research and scientific papers
Iron-catalyzed chemoselective hydride transfer reactions
Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information, (2021/06/07)
A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.
From Celecoxib to a Novel Class of Phosphodiesterase 5 Inhibitors: Trisubstituted Pyrazolines as Novel Phosphodiesterase 5 Inhibitors with Extremely High Potency and Phosphodiesterase Isozyme Selectivity
Abdel-Halim, Mohammad,Sigler, Sara,Racheed, Nora A. S.,Hefnawy, Amr,Fathalla, Reem K.,Hammam, Mennatallah A.,Maher, Ahmed,Maxuitenko, Yulia,Keeton, Adam B.,Hartmann, Rolf W.,Engel, Matthias,Piazza, Gary A.,Abadi, Ashraf H.
supporting information, p. 4462 - 4477 (2021/05/04)
A ligand-based approach involving systematic modifications of a trisubstituted pyrazoline scaffold derived from the COX2 inhibitor, celecoxib, was used to develop novel PDE5 inhibitors. Novel pyrazolines were identified with potent PDE5 inhibitory activit
Green, rapid, and highly efficient syntheses of α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen–Schmidt condensation catalyzed by MoCl5
Bakhshi, Reza,Zeynizadeh, Behzad,Mousavi, Hossein
, p. 623 - 637 (2019/08/26)
A new, green, and highly efficient protocol for the expeditious preparation of some α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones via a simple microwave-assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent-free conditions, simple operation, use of a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.
Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes
Zhang, Yanbin,Jin, Ruiwen,Pan, Guangxing,Guo, Hao
supporting information, p. 11621 - 11624 (2020/10/19)
Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic cyclization of alkynes using non-nucleophilic alkyls as the nucleophile is reported. Upon photoexcitation, o-alkylphenyl alkynyl ketones can be transferred into (E)-photoenols. Thus, a nucleophilic methylene is formed from the non-nucleophilic alkyl. An AlCl3 catalyst can stabilize the (E)-photoenol intermediate and facilitate further intramolecular nucleophilic cyclization. DFT calculations indicated that the AlCl3-catalyzed cyclization is the regioselectivity determining step.
In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
Jung, Hee Jin,Noh, Sang Gyun,Park, Yujin,Kang, Dongwan,Chun, Pusoon,Chung, Hae Young,Moon, Hyung Ryong
, p. 1255 - 1264 (2019/11/11)
Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thi
Synthesis and characterization of novel indanone-based spiro-dihydrobenzofuran derivatives
Güdere, Meliha Burcu,Dürü, Ne?e,Budak, Yakup,Ceylan, Mustafa
, p. 1445 - 1457 (2019/11/02)
In this study, the synthesis and characterization of novel indanone-based spiro-dihydrobenzofuran derivatives were examined. Firstly, chalcone-like compounds 4a–k, (E) -2-benzylidene-2,3-dihydro-1 H -inden-1-one derivatives, were synthesized by the base-c
Synthesis of benzylidenecycloalkan-1-ones and 1,5-diketones under Claisen–Schmidt reaction: Influence of the temperature and electronic nature of arylaldehydes
Lanta?o, Beatriz,Aguirre, José M.,Drago, Eleonora V.,Bollini, Mariela,de la Faba, Diego J.,Mufato, Jorge D.
supporting information, p. 2202 - 2214 (2017/11/20)
Herein, we present the results of the influence of reaction temperature and the electronic nature of arylaldehydes in the reactions of benzocycloalkan-1-ones and arylaldehydes under classical Claisen–Schmidt condensation conditions. The products obtained, 2-arylidene derivatives of benzocycloalkan-1-ones and/or spiropolycyclic-1,5-diketones through multicomponent reactions, depended on the electronic nature of arylaldehyde and the reaction temperature. Besides, under identical conditions, 2-arylideneindan-1-ones afforded bis-indane-1,5-diketones through a process that involves Michael addition reaction, which is also dependent on the temperature. Theoretical studies using density-functional theory allowed understanding the chemical reactivity and the site selectivity of α,β-enones used in this work through the calculation of global and local electrophilicity on C–β. Both the electrophilicity of C-β and the temperature led the course of reaction toward the formation of aldol condensation, aldol condensation/Michael addition, and aldol condensation/dimerization products. This work is the first to perform the structural and configurational assignments of bis-indane-1,5-diketones.
Michael addition of malononitrile to indenones: Synthesis and characterization of 2-(1-oxo-2,3-dihydro-1H-inden-2-yl) (aryl)(methyl)malononitrile derivatives
?ahin, Betül,Gürdere, Meliha Burcu,Ceylan, Mustafa
, p. 1090 - 1095 (2017/05/25)
Indanones 3 were prepared from the reaction of indanone (1) with corresponding benzaldehyde derivatives 2, as described in the literature. Then, indenones 3 were subjected to KOtBu-catalyzed Michael addition with malononitrile to give a mixture of diaster
Catalytic enantioselective cascade Michael/cyclization reaction of 3-isothiocyanato oxindoles with exocyclic α,β-unsaturated ketones: En route to 3,2′-pyrrolidinyl bispirooxindoles
Kayal, Satavisha,Mukherjee, Santanu
supporting information, p. 10175 - 10179 (2016/11/17)
Cascade Michael/cyclization reactions between 3-isothiocyanato oxindoles and exocyclic α,β-unsaturated ketones are shown to proceed efficiently in the presence of a quinine-derived tertiary amino-squaramide catalyst and furnish 3,2′-pyrrolidinyl bispirooxindoles containing two spiro-quaternary and three contiguous stereocenters as a single diastereomer with excellent enantioselectivities (up to 99:1 er).
Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides
Gul, Halise Inci,Tugrak, Mehtap,Sakagami, Hiroshi,Taslimi, Parham,Gulcin, Ilhami,Supuran, Claudiu T.
, p. 1619 - 1624 (2016/10/09)
A series of new 4-(3-(4-substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides (7–12) was synthesized starting from 2-(4-substitutedbenzylidene)-2,3-dihydro-1H-inden-1-one (1–6) and 4-hydrazinobenzenesulfonamide. The substituted
