3969-09-3Relevant articles and documents
Formation of Oxazoles from Elusive Gold(I) α-Oxocarbenes: A Mechanistic Study
Schulz, Ji?í,Ja?ík, Juraj,Gray, Andrew,Roithová, Jana
, p. 9827 - 9834 (2016)
The gold(I) catalyzed reaction between phenylacetylene, pyridine N-oxide and acetonitrile leading, via a putative gold-α-oxocarbene intermediate, towards an oxazole product has been investigated. A novel mass spectrometric method called “delayed reactant
Water Can Accelerate Homogeneous Gold Catalysis
Hashmi, A. Stephen K.,Rudolph, Matthias,Stein, Philipp M.
supporting information, p. 4264 - 4271 (2021/08/03)
A selection of gold-catalyzed reactions was examined in a kinetic study on the influence of water on the rate constant. Two intramolecular reactions and one intermolecular reaction, which proceed via proton transfer and/or protodeauration steps, were inve
Divergent Conversion of N-Acyl-isoxazol-5(2 H)-ones to Oxazoles and 1,3-Oxazin-6-ones Using Photoredox Catalysis
Mei, Mingjing,Anand, Devireddy,Zhou, Lei
supporting information, p. 3548 - 3553 (2019/05/24)
The fragmentation of N-acyl-isoxazol-5-ones using visible light photoredox catalysis has been disclosed. The catalyst-controlled divergent mechanisms, namely the oxidative and reductive quenching catalytic cycle, are utilized. Various oxazoles and 1,3-oxazin-6-ones are selectively obtained from the same isoxazol-5-one skeleton under mild conditions.
Homogeneous and Nanoparticle Gold-Catalyzed Hydrothiocyanation of Haloalkynes
Zeng, Xiaojun,Chen, Bocheng,Lu, Zhichao,Hammond, Gerald B.,Xu, Bo
supporting information, p. 2772 - 2776 (2019/04/30)
The first homogeneous and heterogeneous nanoparticle gold-catalyzed addition of sulfur nucleophiles to alkynes was developed. More specifically, gold-catalyzed hydrothiocyanation of haloalkynes gave good yields and good stereoselectivity of vinyl thiocyanates. Furthermore, a sulfur-based gold catalyst (PPh3AuSCN) has shown a unique reactivity in gold-catalyzed reactions such as the cyclization of N-propargylic amides.
Strategic Approach on N-Oxides in Gold Catalysis – A Case Study
Schie?l, Jasmin,Stein, Philipp M.,Stirn, Judith,Emler, Kirsten,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 725 - 738 (2018/10/20)
An extensive kinetic study of selected key reactions of (oxidative) gold catalysis concentrates on the decrease of the catalytic activity due to inhibition of the gold(I) catalyst caused by pyridine derivatives that are obtained as by-products if N-oxides are applied as oxygen donors. The choice of the examined pyridine derivatives and their corresponding N-oxides has been made regardless of their commercial availability; particular attention has been paid to the practical benefit which up to now has been neglected in most of the reaction screenings. The test reactions were monitored by GC and 1H NMR spectroscopy. The received reaction constants provide information concerning a correlation between the electronic structure of the heterocycle and the catalytic activity. Based on the collected kinetic data, it was possible to develop a basic set of three N-oxides which have to be taken into account in further oxidative gold(I)-catalyzed reactions. (Figure presented.).
1,3-Oxazole-based selective picomolar inhibitors of cytosolic human carbonic anhydrase II alleviate ocular hypertension in rabbits: Potency is supported by X-ray crystallography of two leads
Ferraroni, Marta,Lucarini, Laura,Masini, Emanuela,Korsakov, Mikhail,Scozzafava, Andrea,Supuran, Claudiu T.,Krasavin, Mikhail
, p. 4560 - 4565 (2017/10/06)
Two lead 1,3-oxazole-based carbonic anhydrase inhibitors (CAIs) earlier identified as selective, picomolar inhibitors of hCA II (a cytosolic target for treatment of glaucoma) have been investigated further. Firstly, they were found to be conveniently synt
Base-Induced Transformation of 2-Acyl-3-alkyl-2H-azirines to Oxazoles: Involvement of Deprotonation-Initiated Pathways
Ning, Yingtang,Otani, Yuko,Ohwada, Tomohiko
, p. 6313 - 6326 (2017/06/23)
An experimental study of base-induced transformation reaction of 2-acyl-3-alkyl-2H-azirines to oxazoles indicated that a deprotonation-initiated mechanism is involved, in addition to nucleophilic addition to the imine functionality. Calculations suggested
A Heterogeneous Gold(I)-Catalyzed [2 + 2 + 1] Annulation of Terminal Alkynes, Nitriles, and Oxygen Atoms Leading to 2,5-Disubstituted Oxazoles
Yang, Weisen,Zhang, Rongli,Yi, Feiyan,Cai, Mingzhong
, p. 5204 - 5211 (2017/05/24)
The first heterogeneous gold(I)-catalyzed [2 + 2 + 1] annulation of terminal alkynes, nitriles, and oxygen atoms has been achieved by using an MCM-41-immobilized phosphine-gold(I) complex as catalyst and 8-methylquinoline N-oxide as oxidant under mild conditions, yielding a variety of 2,5-disubstituted oxazoles in good to excellent yields with broad substrate scope. The new heterogeneous gold(I) catalyst can easily be recovered by simple filtration of the reaction solution and recycled for at least eight times without significant loss of activity.
METHOD FOR PRODUCING OXAZOLE COMPOUND
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Paragraph 0049;0053-0054, (2016/10/10)
PROBLEM TO BE SOLVED: To provide a method for producing an oxazole compound which makes it possible to obtain an oxazole compound inexpensively and safely. SOLUTION: A ketone compound, a nitrile compound, an iodinating agent, an oxidizing agent and an acid catalyst are mixed for a reaction to obtain an oxazole compound. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPOandINPIT
Stable yet reactive cationic gold catalysts with carbon based counterions
Zeng, Xiaojun,Liu, Shiwen,Xu, Bo
, p. 77830 - 77833 (2018/06/22)
L-Au-[TsC(CN)2] are new cationic gold catalysts with a carbon based counterion, which are widely applicable for gold catalyzed reactions. For reactions which need highly reactive gold catalysts, a Lewis acid co-catalyst can be added to increase
