Di-tert-butyl Ethynylimidodicarbonate as a General Synthon for the β-Aminoethylation of Organic Electrophiles: Application to the Formal Synthesis of Pyrrolidinoindoline Alkaloids (±)-CPC-1 and (±)-Alline

Q2 · CHEMISTRY

Article

Author: Batey, Robert A. ; Hu, Yiwei ; Beveridge, Ramsay E. ; Gregoire, Bruce

The reagent di-tert-butyl ethynylimidodicarbonate is demonstrated as a β-aminoethyl anion synthetic equivalent. It can be used to install ethyleneamine groups by exploiting its terminal alkyne reactivity with common organic electrophiles. Reactions exemplified with this terminal ynimide reagent include additions to imines, aldehydes, ketones, pyridinium salts, Michael acceptors, epoxides, and Pd-catalyzed Sonogashira couplings. Subsequent regioselective [3 + 2] cycloadditions of the alkynyl-imides (ynimides) generate N,N-di-Boc imide-functionalized triazole and isoxazole heterocycles. Reduction of the ynimides with Pd-catalyzed hydrogenation generates ethyleneimides with easily removable N,N-di-Boc-carbamate protecting groups, allowing for a flexible ynimide-based approach to ethyleneamine installation. The utility of this two-step aminoethylation strategy was demonstrated in the short formal syntheses of pyrrolidinoindoline alkaloids (±)-CPC-1 and (±)-alline. Analogously, the reagent (N,N,N')-tri-Boc 2-ethynylhydrazine serves as a β-hydrazinoethyl anion synthetic equivalent.

01 Apr 2016·Neurocritical CareQ3 · MEDICINE

The Prognostic Value of 48-h Continuous EEG During Therapeutic Hypothermia After Cardiac Arrest

Q3 · MEDICINE

Article

Author: Lamanna, Irene ; Lamartine Monteiro, Marta ; Gaspard, Nicolas ; Mavroudakis, Nicolas ; Depondt, Chantal ; Vincent, Jean-Louis ; Legros, Benjamin ; Ligot, Noémie ; Naeije, Gilles ; Taccone, Fabio Silvio

BACKGROUNDThe aim of this study was to evaluate the prognostic value of continuous electroencephalogram (cEEG) during the first 48 h following cardiac arrest (CA) in patients treated with targeted temperature management (TTM).METHODSWe reviewed data from 92 comatose post-CA patients over a 6 year-period; cEEG recordings were performed during TTM and restoration of normothermia. EEG findings were divided into four time-periods: 0-8, 8-16, 16-24, and 24-48 h after CA. Background EEG findings were defined as moderate encephalopathy (diffuse slowing with reactivity/variability), severe encephalopathy (diffuse slowing without reactivity/variability), burst suppression or suppression, and dichotomized as malignant (suppression/burst suppression/severe encephalopathy) or benign (moderate encephalopathy). Epileptiform activity was defined as the presence of seizures, sporadic epileptiform discharges, or periodic discharges. Neurological outcome was assessed at 3 months using the cerebral performance categories (CPC) score (good outcome: CPC 1-2).RESULTS26/92 (28%) patients had a good outcome. Malignant patterns were associated with a poor outcome at all time-points, with a high positive predictive value (94-97%) but a poor negative predictive value (44-56%). Epileptiform activity did not influence the prognostic value of EEG patterns. All patients with moderate encephalopathy and seizures or generalized periodic discharges had a poor outcome.CONCLUSIONScEEG can identify patients with poor outcome from the first hours following CA, with limited predictive value for good outcome. Epileptiform activity did not improve the prognostic accuracy of EEG, but seizures and generalized periodic discharges were associated with poor outcome even when developing on a benign EEG pattern.

01 Jan 2014·Organic & Biomolecular ChemistryQ3 · CHEMISTRY

Organocatalytic asymmetric decarboxylative cyanomethylation of isatins using l-proline derived bifunctional thiourea

Q3 · CHEMISTRY

Article

Author: V. Pratap Reddy Gajulapalli ; Venkitasamy Kesavan ; Poopathy Vinayagam

First asymmetric decarboxylative cyanomethylation of isatins is reported herewith using bifunctional thiourea derived from l-proline in good yields and enantioselectivities. This strategy enables the construction of various 3-cyanomethylene substituted 3-hydroxyoxindoles in enantioselective manner. Enantioselective synthesis of CPC-1 alkaloid has been accomplished in fewer steps.

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