- Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature
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Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC·HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales. This journal is
- Nielsen, John,Tung, Truong Thanh
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supporting information
p. 10073 - 10080
(2021/12/10)
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- O-alkyl-N-acyl-N-phenylhydroxylamines as photochemical alkoxy radical precursors
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A simple and efficient technique for the photolysis of alkoxy radical precursors is developed. Irradiation of O-alkyl-N-acyl-N-phenylhydroxylamines, as representative alkoxy radical precursors, with ultraviolet light (254 nm) results in homolytic N-O bond cleavage to generate singlet alkoxy and acylaminyl caged radical pairs. These radicals, depending on the solvent employed, either escape from the cage to form fragmentation products, or undergo in-cage reactions to produce photorearrangement products. The homolytic cleavage of the N-O bond is analyzed using time-dependent density functional theory calculations. The nature of the N-acyl substituent on the O-alkyl-N-acyl-N- phenylhydroxylamines is shown to influence their ability to generate radicals. Furthermore, identification and trapping of the alkoxy radicals is demonstrated. Georg Thieme Verlag Stuttgart · New York.
- Chowdhury, Nilanjana,Anoop, Anakuthil,Singh, N.D. Pradeep
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experimental part
p. 1745 - 1754
(2012/07/27)
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- Tetrazole NK1 receptor antagonists: The identification of an exceptionally potent orally active antiemetic compound
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The medicinal chemistry strategy which led to the identification of GR205171, an orally active non-peptide neurokinin-1 receptor antagonist that is the most potent broad-spectrum antiemetic agent reported to date.
- Armour,Chung,Congreve,Evans,Guntrip,Hubbard,Kay,Middlemiss,Mordaunt,Pegg,Vinader,Ward,Watson
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p. 1015 - 1020
(2007/10/03)
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