1517-01-7Relevant academic research and scientific papers
Facile one-step conversion of ketones into α-azidoketones using [hydroxy(tosyloxy)iodo]benzene and sodium azide in the presence of a phase-transfer catalyst under solvent-free conditions
Kumar, Dalip,Sundaree, Swapna,Rao
, p. 1893 - 1896 (2006)
We have described a one-step, solvent-free synthesis of α-azidoketones from the corresponding ketones that requires relatively benign [hydroxy(tosyloxy) iodo]-benzene reagent, sodium azide, and phase-transfer catalyst at room temperature. Generality of th
Oxidative addition of azide anion to triisopropylsilyl enol ethers: Synthesis of α-azido ketones
Magnus, Phillip,Barth, Lisa
, p. 2777 - 2780 (1992)
Treatment of triisopropysilyl enol ethers with ceric ammonium nitrate/sodium azide at -20°C in acetonitrile gives α-azido ketones in average to good yields (50-80%).
A one step conversion of olefins into α-azidoketones using azidotrimethylsilane-chromium trioxide reagent system
Venkat Ram Reddy,Kumareswaran,Vankar, Yashwant D.
, p. 6751 - 6754 (1995)
α-Azidoketones are conveniently obtained in good yields from the corresponding olefins upon reaction with azidotrimethylsilane-chromium trioxide reagent system.
[Hydroxy(tosyloxy)iodo]benzene mediated α-azidation of ketones
Prakash, Om,Pannu, Kamaljeet,Prakash, Richa,Batra, Anita
, p. 523 - 527 (2006)
Reaction of various ketones with [hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment of the α-tosyloxy ketones thus generated in situ with NaN3 offers a one-pot procedure for the synthesis of α-azido ketones. The HTIB used in this conversion may also be generated in situ by using iodosobenzene in combination with p-toluene-sulphonic acid.
Preparation and chemistry of stable azidoiodinanes: 1-Azido-3,3-bis(trifluoromethyl)-3-(1H)-1,2-benziodoxol and 1-Azido-1,2-benziodoxol-3-(1H)-one
Zhdankin, Viktor V.,Kuehl, Chris J.,Krasutsky, Alexei P.,Formaneck, Mark S.,Bolz, Jason T.
, p. 9677 - 9680 (1994)
Azidoiodinanes 2, 4, 6 can be prepared from benziodoxols 1,3 and trimethylsilyl azide in the form of stable, crystalline compounds. These compounds are potentially useful reagents for electrophilic azidonation of organic substrates. For example, reaction
Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization
Maulide, Nuno,Riomet, Margaux,Roller, Alexander,Zhang, Haoqi
supporting information, (2020/03/24)
Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.
α-N-Heteroarylation and α-Azidation of Ketones via Enolonium Species
More, Atul A.,Pathe, Gulab K.,Parida, Keshaba N.,Maksymenko, Shimon,Lipisa, Yuriy B.,Szpilman, Alex M.
, p. 2442 - 2447 (2018/02/23)
Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated by boron trifluoride, react with a variety of nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4-5 h. Additionally, α-azidation of the enolonium species takes place using trimethylsilyl azide as a convenient source of azide nucleophile.
Synthesis of bicyclic proline derivatives by the aza-Cope-Mannich reaction: Formal synthesis of (±)-acetylaranotin
Belov, Dmitry S.,Ratmanova, Nina K.,Andreev, Ivan A.,Kurkin, Alexander V.
supporting information, p. 4141 - 4147 (2015/10/19)
Herein we suggest an approach to oxygenated bicyclic amino acids based on an aza-Cope-Mannich rearrangement. Seven distinct amino acid scaffolds analogous to the natural products were prepared on a gram scale with precise control of stereochemistry. Successful implementation of our strategy resulted in the formal synthesis of acetylaranotin.
Synthesis ofα-azido ketones and esters using recyclable hypervalent iodine reagent
Telvekar, Vikas N.,Patile, Hemlata V.
experimental part, p. 131 - 135 (2011/02/27)
A simple and mild method for the preparation of αazido ketones and esters using hypervalent iodine reagent, 4,4'-bis-(dichloroiodo)-biphenyl, and sodium azide in 1,4-dioxane is discussed. Advantages of this system are easy workup, recyclable reagent, and
PREPARATION OF DIAZO AND DIAZONIUM COMPOUNDS
-
Page/Page column 28, (2010/06/13)
A method for making diazo-compounds, diazonium salts thereof and other protected forms of these compounds. Diaz-compounds are prepared by reaction of a tertiary phosphine reagent carrying a reactive carbonyl group with an azide. The reaction can also generate an acyl triazene which can be converted thermally or by addition of base to form the diazo-compound or the acyl triazene can be isolated. The method is particularly useful for conversion of azides carrying one or more electron withdrawing groups to diazo-compounds. The method can be carried out in aqueous medium under mild conditions and is particularly useful for conversion of azido sugars to diazo-compound and diazonium salts thereof under physiological conditions. Tertiary phosphine reagents, particularly those that are water-soluble, and precursors for preparation of the reagents are provided.
