3672-48-8Relevant academic research and scientific papers
Cracking under internal pressure: Photodynamic behavior of vinyl azide crystals through N2release
Shields, Dylan J.,Karothu, Durga Prasad,Sambath, Karthik,Ranaweera, Ranaweera A. A. Upul,Schramm, Stefan,Duncan, Alexander,Duncan, Benjamin,Krause, Jeanette A.,Gudmundsdottir, Anna D.,Naumov, Pan?e
, p. 18565 - 18575 (2020/12/01)
When exposed to UV light, single crystals of the vinyl azides 3- azido-1-phenylpropenone (1a), 3-azido-1-(4-methoxyphenyl)propenone (1b), and 3-azido-1-(4-chlorophenyl)propenone (1c) exhibit dramatic mechanical effects by cracking or bending with the release of N2. Mechanistic studies using laser flash photolysis, supported by quantum mechanical calculations, show that each of the vinyl azides degrades through a vinylnitrene intermediate. However, despite having very similar crystal packing motifs, the three compounds exhibit distinct photomechanical responses in bulk crystals. While the crystals of 1a delaminate and release gaseous N2 indiscriminately under paraffin oil, the crystals of 1b and 1c visibly expand, bend, and fracture, mainly along specific crystallographic faces, before releasing N2. The photochemical analysis suggests that the observed expansion is due to internal pressure exerted by the gaseous product in the crystal lattices of these materials. Lattice energy calculations, supported by nanoindentation experiments, show significant differences in the respective lattice energies. The calculations identify critical features in the crystal structures of 1b and 1c where elastic energy accumulates during gas release, which correspond to the direction of the observed cracks. This study highlights the hitherto untapped potential of photochemical gas release to elicit a photomechanical response and motility of photoreactive molecular crystals.
Preparation method of isoxazole derivative
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Paragraph 0084-0089, (2019/12/02)
The invention relates to a preparation method of an isoxazole derivative, which comprises the following steps of mixing an propargyl alcohol derivative, a halogen source, an acid and a solvent, and heating to react; adding the hydroxylamine into the react
A novel synthesis of 5-substituted isoxazoles from propargylic amines and N-hydroxyphthalimide
Zhang, Yicheng,Chen, Wei,Jia, Xueshun
supporting information, p. 2181 - 2183 (2018/05/08)
A mild and efficient method for the synthesis of 5-substituted isoxazoles through cyclization of propargylic amines with N-hydroxyphthalimide (NHPI) under metal-free conditions was developed.
An efficient synthesis of isoxazoles and pyrazoles under ultrasound irradiation
Huang, Zhi-Bin,Li, Li-Li,Zhao, Yan-Wei,Wang, Hui-Yuan,Shi, Da-Qing
, p. E309-E313 (2014/11/07)
A series of 5-arylisoxazole and 5-aryl-1H-pyrazole derivatives was synthesized by the reaction of 3-(dimethylamino)-1-arylprop-2-en-1-one with hydroxylamine hydrochloride or hydrazine hydrate under ultrasound irradiation without using any catalyst. This m
A novel synthesis of 1,2,4-oxadiazoles and isoxazoles
Kivrak, Arif,Zora, Metin
, p. 817 - 831 (2014/01/23)
A novel synthesis of 1,2,4-oxadiazoles and isoxazoles is described by utilizing the reactions between amidoximes and α,β-alkynic aldehydes and/or ketones. Conjugate addition products, obtained from amidoximes and α,β-alkynic aldehydes and/or ketones, afford 1,2,4-oxadiazoles and isoxazoles when treated with bases and acids, respectively. 1,2,4-Oxadiazoles can also be synthesized directly from amidoximes and α,β-alkynic aldehydes in a one-pot manner under basic conditions. The reactions are general for a variety of starting compounds and tolerate the presence of aryl, heteroaryl and alkyl groups.
Clean and efficient synthesis of isoxazole derivatives in aqueous media
Dou, Guolan,Xu, Pan,Li, Qiang,Xi, Yukun,Huang, Zhibin,Shi, Daqing
, p. 13645 - 13653 (2014/01/06)
A series of 5-arylisoxazole derivatives were synthesized via the reaction of 3-(dimethyl-amino)-1-arylprop-2-en-1-ones with hydroxylamine hydrochloride in aqueous media without using any catalyst. This method has the advantages of easier work-up, mild rea
Palladium catalyzed carbonylative Heck reaction affording monoprotected 1,3-ketoaldehydes
Gogsig, Thomas M.,Nielsen, Dennis U.,Lindhardt, Anders T.,Skrydstrup, Troels
supporting information; experimental part, p. 2536 - 2539 (2012/08/14)
The direct carbonylative palladium catalyzed synthesis of monoprotected 1,3-ketoaldehydes is reported starting from aryl iodides applying near stoichiometric amounts of carbon monoxide. Besides representing platforms for a variety of heterocyclic structures, these motives serve as viable precursors for the highly relevant aryl methyl ketones. The presented strategy can also be adapted for the facile and efficient incorporation of 13C-labeled carbon monoxide.
Reaction of β-dimethylaminovinyl ketones with hydroxylamine: A simple and useful method for synthesis of 3- and 5-substituted isoxazoles
Rosa, Fernanda A.,Machado, Pablo,Bonacorso, Helio G.,Zanatta, Nilo,Martins, Marcos A. P.
, p. 879 - 885 (2008/09/21)
(Chemical Equation Presented) The regioselective synthesis of 3- and 5-substituted-isoxazoles from the reaction of β-dimethylaminovinyl ketones [R-C(O)CH=CH-NMe2, where R = Ph, MeO-4-C6H4, F-4-C6H4, C
Identification and optimisation of 5-amino-7-aryldihydro-1,4-diazepines as 5-HT2A ligands
Swain, Christopher J.,Teran, Ana,Maroto, Marta,Cabello, Angeles
, p. 6058 - 6062 (2007/10/03)
A several series of low molecular weight 5-HT2A leads were identified from an analysis of HTS data, the exploration of SAR and optimization of one series using parallel synthesis are described, affording compound 22 (5-HT2A IC50 1.1 nM).
Pyrazole and Isoxazole Derivatives as New, Potent, and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors
Nakamura, Toshio,Sato, Masakazu,Kakinuma, Hiroyuki,Miyata, Noriyuki,Taniguchi, Kazuo,Bando, Kagumi,Koda, Ayumi,Kameo, Kazuya
, p. 5416 - 5427 (2007/10/03)
In a previous paper, we reported the N-hydroxyformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor. Despite its attraction as a potential therapeutic agent for cerebral diseases, the preparation of an injectable formulation
