Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, andN-Methoxyamides

2014 ◽  
Vol 20 (52) ◽  
pp. 17565-17571 ◽  
Author(s):  
Minami Nakajima ◽  
Yukiko Oda ◽  
Takamasa Wada ◽  
Ryo Minamikawa ◽  
Kenji Shirokane ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Tertiary Amides ◽  
Secondary Amides

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.

ChemInform Abstract: Chemoselective Reductive Nucleophilic Addition to Tertiary Amides, Secondary Amides, and N-Methoxyamides.

ChemInform ◽  
2015 ◽  
Vol 46 (22) ◽  
pp. no-no
Author(s):  
Minami Nakajima ◽  
Yukiko Oda ◽  
Takamasa Wada ◽  
Ryo Minamikawa ◽  
Kenji Shirokane ◽  
...  
Keyword(s):  
Nucleophilic Addition ◽  
Tertiary Amides ◽  
Secondary Amides

scholarly journals Iridium-catalyzed Reductive Nucleophilic Addition to Tertiary Amides

2019 ◽  
Vol 48 (9) ◽  
pp. 1138-1141 ◽  
Author(s):  
Yoshito Takahashi ◽  
Takaaki Sato ◽  
Noritaka Chida
Keyword(s):  
Nucleophilic Addition ◽  
Tertiary Amides

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.

Iridium-Catalyzed Reductive Nucleophilic Addition to Secondary Amides

2018 ◽  
Vol 20 (18) ◽  
pp. 5705-5708 ◽  
Author(s):  
Yoshito Takahashi ◽  
Risa Yoshii ◽  
Takaaki Sato ◽  
Noritaka Chida
Keyword(s):  
Nucleophilic Addition ◽  
Secondary Amides

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...

Chemoselective reduction of tertiary amides by 1,3-diphenyldisiloxane (DPDS)

Synthesis ◽  
2021 ◽  
Author(s):  
Travis Hammerstad ◽  
Pooja V. Hegde ◽  
Kathleen J. Wang ◽  
Courtney Aldrich
Keyword(s):  
Environmental Impact ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Safety Profile ◽  
Room Temperature ◽  
Reaction Conditions ◽  
Excellent Safety Profile ◽  
Set Up ◽  
Tertiary Amides ◽  
Secondary Amides

A convenient procedure for the chemoselective reduction of tertiary amides at room temperature in the presence of air and moisture using 1,3-diphenyldisiloxane (DPDS) has been developed. The reaction conditions are tolerant of a great number of functional groups including esters, nitriles, secondary amides, carbamates, sulfoxides, sulfones, sulfonyl fluorides, halogens, aryl-nitro groups, and arylamines. The conditions reported are the mildest to date and utilize EtOAc, a preferred solvent given its excellent safety profile and lower environmental impact. The ease of set up and broad chemoselectivity make this method attractive for organic synthesis. These results further demonstrate the utility of DPDS as a selective reducing agent.

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