Selective reduction of secondary amides to amines in the presence of tertiary amides

1999 ◽  
Vol 40 (4) ◽  
pp. 643-644 ◽  
Author(s):  
Byung H. Lee ◽  
Michael F. Clothier
Keyword(s):  
Selective Reduction ◽  
Tertiary Amides ◽  
Secondary Amides

Hydride Reductions of 1H-Pyrrolo[2,1-c][1,4]-benzodiazepine-5,11-diones: Selective Reduction of Secondary Amides to Carbinolamines

1998 ◽  
Vol 51 (12) ◽  
pp. 1121 ◽  
Author(s):  
Andrew G. Katsifis ◽  
Meredith E. McPhee ◽  
Damon D. Ridley
Keyword(s):  
Selective Reduction ◽  
Secondary Amide ◽  
Tertiary Amide ◽  
Secondary Amides

For the syntheses of radiolabelled pyrrolo[1,4]benzodiazepine antitumour antibiotics we required a method in which the unstable carbinolamine functionality was introduced prior to the radiolabel. In turn this required the selective reduction of a secondary amide in the presence of, inter alia, a tertiary amide. We report methods which can be used to achieve this outcome in a series of 1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones.

Spectroscopic studies of the electrophilic activation of amides with triflic anhydride and pyridine

2001 ◽  
Vol 79 (11) ◽  
pp. 1694-1703 ◽  
Author(s):  
André B Charette ◽  
Michel Grenon
Keyword(s):  
Spectroscopic Studies ◽  
Initial Reaction ◽  
Spectroscopic Techniques ◽  
Nmr Study ◽  
Acidic Conditions ◽  
Electrophilic Activation ◽  
Tertiary Amides ◽  
Secondary Amides

The reaction of amides with trifluoromethanesulfonic (triflic) anhydride in the presence of pyridine was thoroughly investigated by NMR spectroscopic techniques. Different pyridinium intermediates were generated from secondary amides, tertiary amides with enolizable protons, and tertiary amides lacking enolizable protons. It was found that the actual triflating reagent is N-(trifluoromethylsulfonyl)pyridinium triflate 11 which is formed by the initial reaction of triflic anhydride with pyridine. The alcoholysis of these intermediates yields O-alkyliminium ethers which can then be easily hydrolyzed under mild acidic conditions to the corresponding esters.Key Words: amides, triflic anhydride, pyridinium intermediates, NMR study.

scholarly journals Understanding the remarkable difference in liquid crystal behaviour between secondary and tertiary amides: the synthesis and characterisation of new benzanilide-based liquid crystal dimers.

2021 ◽  
Author(s):  
Corrie T. Imrie ◽  
Grant James Strachan ◽  
William T. Harrison ◽  
John M. D. Storey
Keyword(s):  
Liquid Crystal ◽  
Remarkable Difference ◽  
Nematic Phases ◽  
Tertiary Amides ◽  
Secondary Amides

A number of liquid crystal dimers have been synthesised and characterised containing secondary or tertiary (N-methyl) benzanilide-based mesogenic groups. The secondary amides all form nematic phases, and we present the...

Total synthesis of complex alkaloids by nucleophilic addition to amides

2018 ◽  
Vol 16 (21) ◽  
pp. 3864-3875 ◽  
Author(s):  
Takaaki Sato ◽  
Makoto Yoritate ◽  
Hayato Tajima ◽  
Noritaka Chida
Keyword(s):  
Total Synthesis ◽  
Nucleophilic Addition ◽  
Recent Progress ◽  
Nucleophilic Additions ◽  
Tertiary Amides ◽  
Secondary Amides

This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions toN-alkoxyamides, tertiary amides and secondary amides.

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