5706-17-2Relevant academic research and scientific papers
Iridium-catalyzed chemoselective transfer hydrogenation of α, β-unsaturated ketones to saturated ketones in water
Chen, Jinxun,Chen, Yongsheng,Cui, Xiaofeng,Jiang, Xiaolan,Liu, Qixing,Zhou, Haifeng
supporting information, (2022/01/24)
A chemoselective iridium-catalyzed transfer hydrogenation of α, β-unsaturated ketones was realized in water. The C[dbnd]C double bonds of 2-benzylidene indanones and analogues were hydrogenated exclusively catalyzed by an iridium complex (0.1 mol%) bearin
I2/TBHP mediated diastereoselective synthesis of spiroaziridines
Ashitha, Kizhakkan Thiruthi,Vinaya, Puthiya Purayil,Krishna, Ajay,Vincent, Deepthy Cheeran,Jalaja, Renjitha,Varughese, Sunil,Somappa, Sasidhar Balappa
supporting information, p. 1588 - 1593 (2020/03/06)
Eventhough spiroheterocycles are considered as emerging drug candidates, synthesis of spiroaziridines has not been well explored so far. Herein, we disclose an efficient I2/TBHP mediated diastereoselective synthesis of N-alkyl spiroaziridines from primary amines and easily accessible α,β-unsaturated ketones. The reaction is also compatible for the synthesis of 2-aroylaziridines.
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.
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.
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
Discovery and structure-activity relationship studies of 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives as a novel class of potential therapeutics for inflammatory bowel disease
Kadayat, Tara Man,Banskota, Suhrid,Gurung, Pallavi,Bist, Ganesh,Thapa Magar, Til Bahadur,Shrestha, Aarajana,Kim, Jung-Ae,Lee, Eung-Seok
supporting information, p. 575 - 597 (2017/06/23)
To develop effective therapeutics for inflammatory bowel disease (IBD), 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives, were designed and synthesized and their structure-activity relationships (SAR) were investigated. Compounds 7, 25, 26, 32, 39, 41, 52, 54, and 55 showed potent inhibitory effect (>70%) on the TNF-α-induced adhesion of monocytes to colon epithelial cells, which is one of the hallmark events leading to IBD. Such inhibitory activity of the compounds correlated with their suppressive activities against the TNF-α-induced production of ROS; ICAM-1 and MCP-1 expression, critical molecules involved in monocyte-epithelial adhesion; and NF-κB transcriptional activity. In addition, compounds 41 and 55 significantly suppressed the lipopolysaccharide (LPS)-induced expression of the TNF-α gene, with compound 55 showing better efficacy. This inhibition of TNF-α expression by compounds 41 and 55 corresponded to their additional inhibitory activity against AP-1 transcriptional activity, which is another transcription factor required for high level TNF-α expression. The strong inhibitory activity of compound 55 against an in vivo colitis model was confirmed by its dose-dependent inhibitory activity in a rat model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis, demonstrating compound 55 as a new potential candidate for the development of therapeutics against IBD.
Asymmetric bio- and chemoreduction of 2-benzylidenecyclopentanone derivatives
?tefane, Bogdan,Gro?elj, Uro?,Svete, Jurij,Po?gan, Franc
, p. 727 - 736 (2018/01/17)
Highly efficient asymmetric reduction of 2-benzylidenecyclopentanone derivatives to give the respective exocyclic allylic alcohols in ee's up to 96% was performed with chiral oxazaborolidine-based catalysts. Complete enantioselectivity furnishing (S)-conf
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
p-TSA-promoted syntheses of 5H-benzo[h]thiazolo[2,3-b]quinazoline and indeno[1,2-d]thiazolo[3,2-a]pyrimidine analogs: Molecular modeling and in vitro antitumor activity against hepatocellular carcinoma
Keshari, Amit K.,Singh, Ashok K.,Raj, Vinit,Rai, Amit,Trivedi, Prakruti,Ghosh, Balaram,Kumar, Umesh,Rawat, Atul,Kumar, Dinesh,Saha, Sudipta
, p. 1623 - 1642 (2017/06/19)
In our efforts to address the rising incidence of hepatocellular carcinoma (HCC), we have made a commitment to the synthesis of novel molecules to combat Hep-G2 cells. A facile and highly efficient one-pot, multicomponent reaction has been successfully de
Synthesis of highly functionalized indeno[1,2-b]furans
Dutta, Leema,Bhuyan, Pulak J.
, p. 3545 - 3548 (2017/10/06)
Some novel functionalized indeno[1,2-b]furans were synthesized from the reaction of indandione/indanone and aldehydes at room temperature followed by the reaction of the Knoevenagel condendensed intermediate with 4-hydroxycoumarins in the presence of iodi
