89530-34-7Relevant academic research and scientific papers
Propargylation of CoQ0 through the Redox Chain Reaction
Mlynarski, Jacek,Pawlowski, Robert,Stodulski, MacIej
, (2022/01/04)
An efficient catalytic propargylation of CoQ0 is described by employing the cooperative effect of Sc(OTf)3 and Hantzsch ester. It is suggested to work through the redox chain reaction, which involves hydroquinone and dimeric propargylic moiety intermediates. A broad range of propargylic alcohols can be converted into the appropriate derivatives of CoQ0 containing triple bonds in good to excellent yields. The mechanism of the given transformation is also discussed.
Multisubstituted pyrazole synthesis via [3?+?2] cycloaddition/rearrangement/N[sbnd]H insertion cascade reaction of α-diazoesters and ynones
Feng, Xiaoming,Liu, Xiaohua,Zeng, Zi,Zhao, Peng
supporting information, p. 132 - 135 (2020/12/21)
The cascade reactions of alkyl α-diazoesters and ynones using Al(OTf)3 as the catalyst are described. A series of 4-substituted pyrazoles were obtained via [3 + 2] cycloaddition, 1,5-ester shift, 1,3-H shift, and N[sbnd]H insertion process. Deuterium labelling experiments, kinetic studies and control experiments were carried out for the rationalization of the mechanism.
Regioselective Synthesis of Multifunctional Allylic Amines; Access to Ambiphilic Aziridine Scaffolds
McLaughlin, Mark G.,Roberts, Dean D.
supporting information, p. 4463 - 4467 (2021/06/28)
We describe, for the first time, a highly regioselective hydrosilylation of propargylic amines. The reaction utilizes a PtCl2/XantPhos catalyst system to deliver hydrosilanes across the alkyne to afford multifunctional allylic amines in high yields. The reaction is tolerant to a wide variety of functional groups and provides high value intermediates with two distinct functional handles. The synthetic applicability of the reaction has been shown through the synthesis of diverse ambiphilic aziridines.
New α-Hydroxy-1,2,3-triazoles and 9H-Fluorenes-1,2,3-triazoles: H Synthesis and Evaluation as Glycine Transporter 1 Inhibitors
Buarque, Camilla D.,Guimar?es, Marilia Z.,López?Corcuera, Beatriz,Neto, Jo?o Gon?alves,No?l, Fran?ois,Silva, Rafaela R.,da Silva, Veronica D.
, p. 1258 - 1269 (2020/10/14)
Two series of new compounds containing 1,2,3-triazole moiety were designed as putative GlyT1 inhibitors aiming the discovery of new hits with activity in cognitive disorders. 1,4-Disubstituted α-hydroxy-1,2,3-triazoles were obtained as racemates in moderate to good yields by the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction (click chemistry) as the key step between propargyl alcohols and aryl azides, previously prepared from anilines or boronic acids. Benzo[c]chromene-triazoles were planned to be obtained by palladium-catalyzed C?H activation using [bis(trifluoroacetoxy)iodobenzene] (PhI(TFA)2) of some α-hydroxy-1,2,3-triazoles, since benzo[c]chromenes are also privileged groups with several biological activities, including to the central nervous system. Unexpectedly, 9H-fluorenes-1,2,3-triazoles, instead of benzo[c]chromenetriazoles, were obtained by Friedel-Crafts alkylation reaction. The two series of compounds were tested for inhibition of the glycine transporter (rat GlyT1 isoform) but only the α-hydroxy-1,2,3-triazole 9b was active (half maximal inhibitory concentration (IC50) = 8.0 μM).
Gold-Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)-Additions and 1,2-Carbon Migration
Skaria, Manisha,More, Sayaji Arjun,Kuo, Tung-Chun,Cheng, Mu-Jeng,Liu, Rai-Shung
supporting information, p. 3600 - 3608 (2020/03/04)
This work reports gold-catalyzed iminations of terminal propargyl alcohols with anthranils or isoxazoles to yield E-configured α-amino-2-en-1-ones and -1-als with complete chemoselectivity. These catalytic iminations occur exclusively with C(1)-nucleophilic additions on terminal alkynes, in contrast to a typical C(2)-route. For 3,3-dialkylprop-1-yn-3-ols, a methyl substituent is superior to long alkyl chains as the 1,2-migration groups toward α-imino gold carbenes. For secondary prop-1-yn-3-ols, phenyl, vinyl, and cyclopropyl substituents are better than hydrogen as the migrating groups, obviating typical gold carbene reactions. DFT calculations have been performed to rationalize the observed C(1)-regioselectivity and the preferable cyclopropyl migration based on gold carbene pathways.
A Domino Strategy for the Synthesis of 2H-Pyrans from Propargyl Vinyl Ethers
Tejedor, David,Delgado-Hernández, Samuel,Diana-Rivero, Raquel,Díaz-Díaz, Abián,García-Tellado, Fernando
, p. 1784 - 1790 (2019/02/19)
Stable monocyclic 2H-pyrans are synthesized from readily available tertiary propargyl vinyl ethers via a metal-free all-pericyclic domino manifold involving a sequential propargyl Claisen rearrangement/[1,3]H-shift/oxa-6π electrocyclization set of reactions. The wide scope of this protocol is exemplified by the synthesis of 21 different 2H-pyrans incorporating a varied substitution pattern at the ring.
Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides
Andna, Lucile,Miesch, Laurence
supporting information, p. 5688 - 5692 (2019/06/19)
An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.
Access to Enantioenriched Organosilanes from Enals and β-Silyl Enones: Carbene Organocatalysis
Zhang, Yuxia,Huang, Jie,Guo, Yingying,Li, Lin,Fu, Zhenqian,Huang, Wei
supporting information, p. 4594 - 4598 (2018/03/21)
Herein, an efficient route to enantioenriched organosilanes, containing two consecutive stereogenic centers, from enals and β-silyl enones under carbene organocatalysis is described. Under mild reaction conditions, this transition-metal-free strategy exhibits a broad substrate scope, and excellent diastereo- and enantioselectivity.
Cascade and Effective Syntheses of Functionalized Tellurophenes
Karapala, Vamsi Krishna,Shih, Hong-Pin,Han, Chien-Chung
supporting information, p. 1550 - 1554 (2018/03/23)
A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-1-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.
Gold(I)-Catalyzed Tandem Cycloisomerization and Fluorination of 1,3(4)-Enyne Esters with NFSI: One-Pot Assembly of 5-Fluoro- Cyclopentenones
Chen, Xianxiao,Zhou, Yuanyuan,Hong, Mei,Ling, Yuan,Yin, Dongliang,Wang, Shifa,Zhang, Xiaoxiang,Rao, Weidong
supporting information, p. 3700 - 3708 (2018/09/12)
An efficient synthetic approach for the synthesis of 5-fluoro-cyclopentenones containing a fluorine-substituted carbon stereocenter that relies on gold(I)-catalyzed cycloisomerization and fluorination sequence of 1,3(4)-enyne esters with N-fluorbenzensulfonimide (NFSI) is described. This tandem transformation exhibited a broad substrate scope and excellent functional group compatibility, providing a novel protocol for rapid assembly 5-fluoro-cyclopentenones in good to excellent yields under mild reaction conditions. The mechanistic studies revealed that the transformation involves a gold-catalyzed cycloisomerization and electrophilic fluorination cascade to give the 5-fluoro-cyclopentenones. (Figure presented.).
