Asymmetric Deoxygenative Alkynylation of Tertiary Amides Enabled by Iridium/Copper Bimetallic Relay Catalysis

2021 ◽  
Author(s):  
Zhaokun Li ◽  
Feng Zhao ◽  
Wei Ou ◽  
Pei-Qiang Huang ◽  
Xiaoming Wang
Keyword(s):  
Tertiary Amides

Lithium compound catalyzed deoxygenative hydroboration of primary, secondary and tertiary amides

2021 ◽  
Vol 50 (7) ◽  
pp. 2354-2358
Author(s):  
Milan Kumar Bisai ◽  
Kritika Gour ◽  
Tamal Das ◽  
Kumar Vanka ◽  
Sakya S. Sen
Keyword(s):  
Lithium Compound ◽  
Tertiary Amides

A very simple and readily accessible lithium compound has been employed to catalyze the hydroboration of tertiary, secondary, and primary amides to the corresponding amines.

A synthesis of alkylated 3-aminoisoquinolines and related compounds

1982 ◽  
Vol 35 (7) ◽  
pp. 1391 ◽  
Author(s):  
AJ Liepa
Keyword(s):  
Phosphoryl Chloride ◽  
Tertiary Amides ◽  
Derivatives Of ◽  
Related Compounds ◽  
Selection Of

N,N-Dialkyl derivatives of 3-aminoisoquinoline have been prepared by reaction of nitriles with various arylacetic acid tertiary amides in the presence of phosphoryl chloride. The synthesis has been extended to include a benzoisoquinoline and annulated isoquinolines by the selection of appropriate amide and nitrile precursors.

Preparation of Tertiary Amides from Carbamoyl Chlorides and Organocuprates

2004 ◽  
Vol 6 (21) ◽  
pp. 3703-3706 ◽  
Author(s):  
Laurent Lemoucheux ◽  
Thomas Seitz ◽  
Jacques Rouden ◽  
Marie-Claire Lasne
Keyword(s):  
Tertiary Amides

One-pot synthesis of amides from carboxylic acids activated using thionyl chloride

RSC Advances ◽  
2016 ◽  
Vol 6 (41) ◽  
pp. 34468-34475 ◽  
Author(s):  
A. Leggio ◽  
E. L. Belsito ◽  
G. De Luca ◽  
M. L. Di Gioia ◽  
V. Leotta ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Tertiary Amine ◽  
Thionyl Chloride ◽  
One Pot ◽  
One Pot Synthesis ◽  
Tertiary Amides

We report on a one-pot synthesis of secondary and tertiary amides from carboxylic acids and amines in the presence of a tertiary amine by using thionyl chloride.

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>

Controlling Chemoselectivity in the Lithiation of Substituted Aromatic Tertiary Amides

2004 ◽  
Vol 116 (16) ◽  
pp. 2187-2190 ◽  
Author(s):  
David R. Armstrong ◽  
Sally R. Boss ◽  
Jonathan Clayden ◽  
Robert Haigh ◽  
Basel A. Kirmani ◽  
...  
Keyword(s):  
Tertiary Amides
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