494210-98-9Relevant articles and documents
Rhodium(III)-Catalyzed Oxidative Intramolecular 1,1-Oxyamination of Alkenes with Protected Amino Acids to Produce Oxazoloisoindole-2,5-diones
Takahashi, Hiroto,Nagashima, Yuki,Tanaka, Ken
supporting information, p. 1891 - 1895 (2021/04/05)
It has been established that an electron-deficient bis(ethoxycarbonyl)-substituted cyclopentadienyl (CpE) rhodium(III) complex catalyzes the oxidative intramolecular 1,1-oxyamination of alkenes with N-benzoyl amino acids to produce oxazoloisoindole-2,5-diones. Experimental and theoretical mechanistic studies revealed that this oxidative 1,1-oxyamination proceeds via not the aza-Wacker reaction but the formation of a rhoda(III)oxazolidine initiated by the carboxylic acid-directed N?H bond cleavage.
Enantioselective Lactonization by π-Acid-Catalyzed Allylic Substitution: A Complement to π-Allylmetal Chemistry
Aponick, Aaron,Kizhakkayil Mangadan, Arun Raj,Liu, Ji
supporting information, p. 22224 - 22229 (2021/09/09)
Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non-racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π-acid catalysis. More specifically, a
Intramolecular C-H activation through gold(I)-catalyzed reaction of iodoalkynes
Morn-Poladura, Pablo,Rubio, Eduardo,Gonzlez, Jos M.
supporting information, p. 3052 - 3055 (2015/04/14)
The cycloisomerization reaction of 1-(iodoethynyl)-2-(1-methoxyalkyl)arenes and related 2-alkyl-substituted derivatives gives the corresponding 3-iodo-1-substituted-1H-indene under the catalytic influence of IPrAuNTf2 [IPr = 1,3-bis(2,6-diisopropyl)phenylimidazol-2-ylidene; NTf2 = bis(trifluoromethanesulfonyl)imidate]. The reaction takes place in 1,2-dichloroethane at 80°C, and the addition of ttbp (2,4,6-tritert-butylpyrimidine) is beneficial to accomplish this new transformation in high yield. The overall reaction implies initial assembly of an intermediate gold vinylidene upon alkyne activation by gold(I) and a 1,2-iodine-shift. Deuterium labeling and crossover experiments, the magnitude of the recorded kinetic primary isotopic effect, and the results obtained from the reaction of selected stereochemical probes strongly provide support for concerted insertion of the benzylic C-H bond into gold vinylidene as the step responsible for the formation of the new carbon-carbon bond.
Photocatalytic Dehydrogenative Lactonization of 2-Arylbenzoic Acids
Ramirez, Nieves P.,Bosque, Irene,Gonzalez-Gomez, Jose C.
supporting information, p. 4550 - 4553 (2015/09/28)
A metal-free dehydrogenative lactonization of 2-arylbenzoic acids at room temperature was developed. This work illustrates the first application of visible-light photoredox catalysis in the preparation of benzo-3,4-coumarins, an important structural motif in bioactive molecules. The combination of photocatalyst [Acr+-Mes] with (NH4)2S2O8 as a terminal oxidant provides an economical and environmentally benign entry to different substituted benzocoumarins. Preliminary mechanistic studies suggest that this reaction most likely occurs through a homolytic aromatic substitution pathway.
Pd-catalyzed C-H lactonization for expedient synthesis of biaryl lactones and total synthesis of cannabinol
Li, Yan,Ding, Yan-Jun,Wang, Jian-Yong,Su, Yi-Ming,Wang, Xi-Sheng
supporting information, p. 2574 - 2577 (2013/07/11)
A practical Pd(II)/Pd(IV)-catalyzed carboxyl-directed C-H activation/C-O cyclization to construct biaryl lactones has been developed. The synthetic utility of this new reaction was demonstrated in an atom-economical and operationally convenient total synthesis of the natural product cannabinol from commercially available starting materials, with the newly developed method used for two key steps.
Conception of myeloperoxidase inhibitors derived from flufenamic acid by computational docking and structure modification
Van Antwerpen, Pierre,Prevost, Martine,Zouaoui-Boudjeltia, Karim,Babar, Sajida,Legssyer,Moreau, Patrick,Moguilevsky, Nicole,Vanhaeverbeek, Michel,Ducobu, Jean,Neve, Jean,Dufrasne, Francois
, p. 1702 - 1720 (2008/09/20)
The development of myeloperoxidase (MPO) inhibitors has been conducted using flufenamic acid as a lead compound. Computational docking of the drug and its analogs in the MPO active site was first attempted. Several molecules were then synthesized and assessed using three procedures for the measurement of their inhibiting activity: (i) the taurine assay, (ii) the accumulation of compound II, and (iii) the LDL oxidation by ELISA. Most of the synthesized molecules had an activity in the same range as flufenamic acid but none of them were able to inhibit the MPO-dependent LDL oxidation. The experiments however gave some useful indications for a rational conception of MPO inhibitors.
Practical Synthesis of Aryl Triflates under Aqueous Conditions
Frantz, Doug E.,Weaver, Damian G.,Carey, James P.,Kress, Michael H.,Dolling, Ulf H.
, p. 4717 - 4718 (2007/10/03)
A practical and efficient synthesis of aryl triflates under biphasic basic aqueous conditions is described. The current methodology provides entry into these valuable substrates that omits the use of amine bases and allows facile isolation by s
