404345-06-8Relevant academic research and scientific papers
A versatile tripodal Cu(I) reagent for C-N bond construction via nitrene-transfer chemistry: Catalytic perspectives and mechanistic insights on C-H aminations/amidinations and olefin aziridinations
Bagchi, Vivek,Paraskevopoulou, Patrina,Das, Purak,Chi, Lingyu,Wang, Qiuwen,Choudhury, Amitava,Mathieson, Jennifer S.,Cronin, Leroy,Pardue, Daniel B.,Cundari, Thomas R.,Mitrikas, George,Sanakis, Yiannis,Stavropoulos, Pericles
supporting information, p. 11362 - 11381 (2014/09/17)
A CuI catalyst (1), supported by a framework of strongly basic guanidinato moieties, mediates nitrene-transfer from PhI=NR sources to a wide variety of aliphatic hydrocarbons (C-H amination or amidination in the presence of nitriles) and olefins (aziridination). Product profiles are consistent with a stepwise rather than concerted C-N bond formation. Mechanistic investigations with the aid of Hammett plots, kinetic isotope effects, labeled stereochemical probes, and radical traps and clocks allow us to conclude that carboradical intermediates play a major role and are generated by hydrogen-atom abstraction from substrate C-H bonds or initial nitrene-addition to one of the olefinic carbons. Subsequent processes include solvent-caged radical recombination to afford the major amination and aziridination products but also one-electron oxidation of diffusively free carboradicals to generate amidination products due to carbocation participation. Analyses of metal- and ligand-centered events by variable temperature electrospray mass spectrometry, cyclic voltammetry, and electron paramagnetic resonance spectroscopy, coupled with computational studies, indicate that an active, but still elusive, copper-nitrene (S = 1) intermediate initially abstracts a hydrogen atom from, or adds nitrene to, C-H and C=C bonds, respectively, followed by a spin flip and radical rebound to afford intra- and intermolecular C-N containing products.
Nanocrystalline zinc peroxide mediated unprecedented nitrene transfer: An expeditious access to N-tosylaziridines
Verma, Sanny,Jain, Suman L.
, p. 19830 - 19833 (2013/11/06)
An unprecedented zinc peroxide (ZnO2) assisted synthetic strategy is reported for the synthesis of N-tosylaziridines from alkenes by using N-tosyliminotriphenylphosphorane (Ph3PNTs) as a nitrene transfer reagent under mild reaction conditions. The reaction of zinc peroxide with Ph3PNTs yielded a zinc oxaziridine intermediate which subsequently reacts with alkenes to give corresponding N-tosylaziridines in high to excellent yields. The Royal Society of Chemistry 2013.
ANTIFUNGAL AGENTS
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Page/Page column 61, (2010/04/03)
Novel derivatives of enfumafungin are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antifungal agents and/or inhibitors of (l,3)-β-D-glucan synthase. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs,,as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating and/or preventing fungal infections and associated diseases and conditions.
ANTIFUNGAL AGENTS
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Page/Page column 48, (2010/04/03)
Novel derivatives of enfumafungin are disclosed herein, along with' their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and method of using such compounds as antifungal agents and/or inhibitors of (l,3)-β-D-glucan synthase. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating and/or preventing fungal infections and associated diseases and conditions.
Cobalt-catalyzed efficient aziridination of alkenes
Gao, Guang-Yao,Harden, Jeremiah D.,Zhang, X. Peter
, p. 3191 - 3193 (2007/10/03)
(Chemical Equation Presented) Cobalt porphyrins are capable of catalyzing the aziridination of alkenes with bromamine-T as the nitrene source. Among cobalt complexes of different porphyrins, Co(TDCIPP) is an effective catalyst that can aziridinate a wide
Iron(III) porphyrin catalyzed aziridination of alkenes with bromamine-T as nitrene source
Vyas, Renu,Gao, Guang-Yao,Harden, Jeremiah D.,Zhang, X. Peter
, p. 1907 - 1910 (2007/10/03)
Equation presented. Iron(III) porphyrin complexes Fe(Por)Cl are effective catalysts for aziridination of alkenes using bromamine-T as the nitrene source. The catalytic system can operate under mild conditions with alkenes as limiting reagents. The aziridi
Development of a [3+3] cycloaddition strategy toward functionalized piperidines
Hedley, Simon J.,Moran, Wesley J.,Price, David A.,Harrity, Joseph P. A.
, p. 4286 - 4292 (2007/10/03)
This paper describes a novel route to functionalized piperidines via a formal [3+3] cycloaddition reaction of activated aziridines and palladium-trimethylenemethane (Pd-TMM) complexes. The cycloaddition reaction generally proceeds enantiospecifically with
Enantioselective route to key intermediates in the synthesis of carbocyclic phosphoribosyltransferase transition state analogues
Ahmadian, Mohammad,Khare, Naveen K.,Riordan, James M.,Klon, Anthony E.,Borhani, David W.
, p. 9899 - 9909 (2007/10/03)
The enantioselective preparation of key intermediates in the synthesis of transition state analogues of hypoxanthine-guanine phosphoribosyltransferase, (1S,2S,3R,4R)-4-acetoxymethyl-1-bromomethyl-2,3-isopropylidenedioxy-1- toluenesulfonamidocyclopentane (3a) and the 4-nitrobenzenesulfonamido analogue (3b), are described.
