scholarly journals Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

2021 ◽  
Vol 17 ◽  
pp. 527-539
Author(s):  
Lukáš Marek ◽  
Lukáš Kolman ◽  
Jiří Váňa ◽  
Jan Svoboda ◽  
Jiří Hanusek
Keyword(s):  
Coupling Reaction ◽  
Inhibiting Activity ◽  
Nmr Techniques ◽  
Modular Method ◽  
Tertiary Amides ◽  
Tyrosin Kinase

A highly modular method for the synthesis of (Z)-3-[amino(phenyl/methyl)methylidene]-1,3-dihydro-2H-indol-2-ones starting from easily available 3-bromooxindoles or (2-oxoindolin-3-yl)triflate and thioacetamides or thiobenzamides is described. A series of 49 compounds, several of which have previously been shown to possess significant tyrosin kinase inhibiting activity, was prepared in yields varying mostly from 70 to 97% and always surpassing those obtained by other published methods. The method includes an Eschenmoser coupling reaction, which is very feasible (even without using a thiophile except tertiary amides) and scalable. The (Z)-configuration of all products was confirmed by NMR techniques.

scholarly journals General α-Amino 1,3,4-Oxadiazole Synthesis via Late-Stage Reductive Functionalization of Tertiary Amides and Lactams

2021 ◽  
Author(s):  
Daniel Matheau-Raven ◽  
Darren J. Dixon
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Coupling Reaction ◽  
Reductive Activation ◽  
Mild Conditions ◽  
Drug Molecules ◽  
Drug Conjugates ◽  
Iminium Ion ◽  
Tertiary Amides ◽  
Coupling Partner

An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (<1 mol%) Vaska’s complex (IrCl(CO)(PPh<sub>3</sub>)<sub>2</sub>) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of structurally complex α-amino 1,3,4-oxadiazole architectures were efficiently accessed from diverse carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Brønsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. Furthermore, the high chemoselectivity of the catalytic reductive activation step allowed the late-stage functionalization of 10 drug molecules, including the synthesis of novel heterodiazole-fused drug-drug conjugates.<br>

scholarly journals Tertiary amine synthesis via reductive coupling of amides with Grignard reagents

2017 ◽  
Vol 8 (11) ◽  
pp. 7492-7497 ◽  
Author(s):  
Lan-Gui Xie ◽  
Darren J. Dixon
Keyword(s):  
Tertiary Amine ◽  
Coupling Reaction ◽  
Grignard Reagents ◽  
Reductive Coupling ◽  
Tertiary Amides

A new iridium catalyzed reductive coupling reaction of Grignard reagents and tertiary amides affording functionalised tertiary amine products is described.

scholarly journals General α-Amino 1,3,4-Oxadiazole Synthesis via Late-Stage Reductive Functionalization of Tertiary Amides and Lactams

2021 ◽  
Author(s):  
Daniel Matheau-Raven ◽  
Darren J. Dixon
Keyword(s):  
Carboxylic Acid ◽  
Late Stage ◽  
Coupling Reaction ◽  
Reductive Activation ◽  
Mild Conditions ◽  
Drug Molecules ◽  
Drug Conjugates ◽  
Iminium Ion ◽  
Tertiary Amides ◽  
Coupling Partner

An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (<1 mol%) Vaska’s complex (IrCl(CO)(PPh<sub>3</sub>)<sub>2</sub>) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of structurally complex α-amino 1,3,4-oxadiazole architectures were efficiently accessed from diverse carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Brønsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. Furthermore, the high chemoselectivity of the catalytic reductive activation step allowed the late-stage functionalization of 10 drug molecules, including the synthesis of novel heterodiazole-fused drug-drug conjugates.<br>

Mitochondrial matrix calcium ions regulate energy production in myocardium: A cytochemical study

1990 ◽  
Vol 48 (2) ◽  
pp. 166-167
Author(s):  
W.A. Jacob ◽  
R. Hertsens ◽  
A. Van Bogaert ◽  
M. De Smet
Keyword(s):  
Energy Metabolism ◽  
Calcium Ions ◽  
Energy Production ◽  
Regulation Of Respiration ◽  
Free Calcium ◽  
Mitochondrial Matrix ◽  
Cytochemical Study ◽  
Nmr Techniques

In the past most studies of the control of energy metabolism focus on the role of the phosphorylation potential ATP/ADP.Pi on the regulation of respiration. Studies using NMR techniques have demonstrated that the concentrations of these compounds for oxidation phosphorylation do not change appreciably throughout the cardiac cycle and during increases in cardiac work. Hence regulation of energy production by calcium ions, present in the mitochondrial matrix, has been the object of a number of recent studies.Three exclusively intramitochondnal dehydrogenases are key enzymes for the regulation of oxidative metabolism. They are activated by calcium ions in the low micromolar range. Since, however, earlier estimates of the intramitochondnal calcium, based on equilibrium thermodynamic considerations, were in the millimolar range, a physiological correlation was not evident. The introduction of calcium-sensitive probes fura-2 and indo-1 made monitoring of free calcium during changing energy metabolism possible. These studies were performed on isolated mitochondria and extrapolation to the in vivo situation is more or less speculative.

Isolation of isoflavonoids from Amphimas pterocarpoides and structure elucidation using LC-HRMSn and NMR techniques

Planta Medica ◽  
2010 ◽  
Vol 76 (12) ◽  
Author(s):  
J Tchoumtchoua ◽  
M Halabalaki ◽  
D Njamen ◽  
J Mbanya ◽  
L Skaltsounis
Keyword(s):  
Structure Elucidation ◽  
Nmr Techniques

HERG channel inhibiting activity of Rauvolfia nukuhivensis alkaloid content

Planta Medica ◽  
2014 ◽  
Vol 80 (16) ◽  
Author(s):  
NJ Martin ◽  
EA López ◽  
G Lecellier ◽  
M Nicolas ◽  
C Paetz ◽  
...  
Keyword(s):  
Alkaloid Content ◽  
Herg Channel ◽  
Inhibiting Activity

Substituted Amides of Quinoline Derivatives: Preparation and Their Photosynthesis-inhibiting Activity

2006 ◽  
Author(s):  
Robert Musiol ◽  
Josef Jampilek ◽  
Katarina Kralova ◽  
Dominik Tabak ◽  
Barbara Podeszwa ◽  
...  
Keyword(s):  
Inhibiting Activity ◽  
Quinoline Derivatives
Sign in / Sign up

Export Citation Format

Share Document