Tertiary amide-based Knoevenagel-type reactions: a direct, general, and chemoselective approach to enaminones

2014 ◽  
Vol 50 (63) ◽  
pp. 8761 ◽  
Author(s):  
Pei-Qiang Huang ◽  
Wei Ou ◽  
Kai-Jiong Xiao ◽  
Ai-E Wang
Keyword(s):  
Tertiary Amide

Investigations of Different Chemoselectivities in Primary, Secondary and Tertiary Amide Reactions with Sodium Borohydride

2006 ◽  
Vol 2006 (8) ◽  
pp. 1991-1999 ◽  
Author(s):  
Jie Ren ◽  
Liang-Chun Li ◽  
Ji-Kai Liu ◽  
Hua-Jie Zhu ◽  
Charles U. Pittman
Keyword(s):  
Sodium Borohydride ◽  
Tertiary Amide

scholarly journals Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 2003 ◽  
Author(s):  
Takatsugu Murata ◽  
Tatsuya Kawanishi ◽  
Akihiro Sekiguchi ◽  
Ryo Ishikawa ◽  
Keisuke Ono ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
High Selectivity ◽  
Optically Active ◽  
Acyl Transfer ◽  
Chiral Compounds ◽  
Tertiary Amide

Various optically active 2-hydroxyamide derivatives are produced based on the kinetic resolution of racemic 2-hydroxyamides with a diphenylacetyl component and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst, via asymmetric esterification and acylation. It was revealed that a tertiary amide can be used with this novel protocol to achieve high selectivity (22 examples; s-value reaching over 250). The resulting chiral compounds could be transformed into other useful structures while maintaining their chirality.

Peptidomimetics with tunable tertiary amide bond containing substituted β-proline and β-homoproline

Tetrahedron ◽  
2014 ◽  
Vol 70 (6) ◽  
pp. 1169-1175 ◽  
Author(s):  
Sandip Basu ◽  
Pancham Singh Kandiyal ◽  
Venkata Suresh Kumar Neelamraju ◽  
Harjinder Singh ◽  
Ravi Sankar Ampapathi ◽  
...  
Keyword(s):  
Amide Bond ◽  
Tertiary Amide

scholarly journals Selective Extraction of Platinum(IV) from the Simulated Secondary Resources Using Simple Secondary Amide and Urea Extractants

Separations ◽  
2021 ◽  
Vol 8 (9) ◽  
pp. 139
Author(s):  
Yuki Ueda ◽  
Shintaro Morisada ◽  
Hidetaka Kawakita ◽  
Keisuke Ohto
Keyword(s):  
Electrical Equipment ◽  
Selective Extraction ◽  
Extraction Process ◽  
Secondary Amide ◽  
Separation And Purification ◽  
Secondary Resources ◽  
Tertiary Amide ◽  
Third Phase ◽  
Simulated Effluent ◽  
Secondary Amides

The recycling of rare metals such as platinum (Pt) from secondary resources, such as waste electronic and electrical equipment and automotive catalysts, is an urgent global issue. In this study, simple secondary amides and urea, N-(2-ethylhexyl)acetamide, N-(2-ethylhexyl)octanamide, and 1-butyl-3-(2-ethylhexyl)urea, which selectively extract Pt(IV) from a simulated effluent containing numerous metal ions, such as in an actual hydrometallurgical process, were synthesized and achieved efficient Pt(IV) stripping using only water. Comparison of Pt(IV) extraction behavior with a tertiary amide without N–H moieties suggests that the secondary amides and urea extractants effectively use hydrogen bonding to the hexachloroplatinate anion by N–H moieties. Examining the conditions for the third phase formation revealed that the secondary amide extractant with the longest alkyl chain can be used in the extraction process for a long time without forming any third phase, despite its lower Pt(IV) extraction capacity. The practical trial with simple compounds developed in this study should contribute to the development of Pt separation and purification processes.

Catalytic Transamidation Reactions Compatible with Tertiary Amide Metathesis under Ambient Conditions

2009 ◽  
Vol 131 (29) ◽  
pp. 10003-10008 ◽  
Author(s):  
Nickeisha A. Stephenson ◽  
Jiang Zhu ◽  
Samuel H. Gellman ◽  
Shannon S. Stahl
Keyword(s):  
Ambient Conditions ◽  
Tertiary Amide

scholarly journals The ozonolysis of primary aliphatic amines in fine particles

2008 ◽  
Vol 8 (5) ◽  
pp. 1181-1194 ◽  
Author(s):  
J. Zahardis ◽  
S. Geddes ◽  
G. A. Petrucci
Keyword(s):  
Fine Particles ◽  
Reaction System ◽  
Tropospheric Chemistry ◽  
Ozone Exposure ◽  
Surface Barrier ◽  
Secondary Amide ◽  
Tertiary Amide ◽  
Aerosol Mass ◽  
Criegee Intermediates ◽  
Species Specific

Abstract. The oxidative processing by ozone of the particulate amines octadecylamine (ODA) and hexadecylamine (HDA) is reported. Ozonolysis of these amines resulted in strong NO2– and NO3– ion signals that increased with ozone exposure as monitored by photoelectron resonance capture ionization aerosol mass spectrometry. These products suggest a mechanism of progressive oxidation of the particulate amines to nitroalkanes. Additionally, a strong ion signal at 125 m/z is assigned to the ion NO3– (HNO3). For ozonized mixed particles containing ODA or HDA + oleic acid (OL), with pO3≥3×10–7 atm, imine, secondary amide, and tertiary amide products were measured. These products most likely arise from reactions of amines with aldehydes (for imines) and stabilized Criegee intermediates (SCI) or secondary ozonides (for amides) from the fatty acid. The routes to amides via SCI and/or secondary ozonides were shown to be more important than comparable amide forming reactions between amines and organic acids, using azelaic acid as a test compound. Finally, direct evidence is provided for the formation of a surface barrier in the ODA + OL reaction system that resulted in the retention of OL at high ozone exposures (up to 10−3 atm for 17 s). This effect was not observed in HDA + OL or single component OL particles, suggesting that it may be a species-specific surfactant effect from an in situ generated amide or imine. Implications to tropospheric chemistry, including particle bound amines as sources of oxidized gas phase nitrogen species (e.g.~NO2, NO3), formation of nitrogen enriched HULIS via ozonolysis of amines and source apportionment are discussed.

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.

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