30979-60-3Relevant academic research and scientific papers
Poly(methylhydrosiloxane) as a green reducing agent in organophosphorus-catalysed amide bond formation
Hamstra, Daan F. J.,Lenstra, Danny C.,Koenders, Tjeu J.,Rutjes, Floris P. J. T.,Mecinovi?, Jasmin
supporting information, p. 6426 - 6432 (2017/08/10)
Development of catalytic amide bond formation reactions has been the subject of the intensive investigations in the past decade. Herein we report an efficient organophosphorus-catalysed amidation reaction between unactivated carboxylic acids and amines. Poly(methylhydrosiloxane), a waste product of the silicon industry, is used as an inexpensive and green reducing agent for in situ reduction of phosphine oxide to phosphine. The reported method enables the synthesis of a wide range of secondary and tertiary amides in very good to excellent yields.
TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides
Singh, Garima,Dada, Ravikrishna,Yaragorla, Srinivasarao
supporting information, p. 4424 - 4427 (2016/09/13)
A One-Pot tandem Schmidt–Ritter process for the synthesis of amides has been developed using the super acid as catalyst. The in situ generated aryl/aliphatic nitriles from the reaction of aldehydes and sodium azide in the presence of TfOH and AcOH (Schmidt reaction) react with suitable alcohol (Ritter reaction) to give the amides. For the first time we observed that during the Schmidt process N-acylimides were generated along with nitriles, interestingly these N-acylimides also participated in the Ritter reaction.
The invention of radical reactions. 30. Diazirines as carbon radical traps. Mechanistic aspects and synthetic applications of a novel and efficient amination process
Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Theodorakis, Emmanouil A.,Reibenspies
, p. 8050 - 8059 (2007/10/02)
A number of diazirines were synthesized for the purpose of exploring the addition of a carbon radical to the nitrogen-nitrogen double bond. Carbon radicals, generated from the photolysis of the O-acyl derivatives of N-hydroxy-2-thiopyridone or via radical exchange from the corresponding organotellurides, were shown to add smoothly to the diazirines leading to imines 34. When 3-(trifluoromethyl)-3-phenyldiazirine (13) is used as the trap, the thus formed imines can be easily hydrolyzed to amines. A mechanism that involves dimerization of the diaziridinyl radicals 32 to produce tetraazo intermediates 33 is suggested in accord with variable temperature NMR data for the reaction. Proof for this mechanistic scheme was furthermore obtained by isolation and X-ray structure determination of 33d. The first X-ray structure of a 3-(trifluoromethyl)-3-aryldiazirine is also reported.
Antiviral agents/4th communication: the aromatically substituted carbonic acid amide structure in potentically virustatic compounds (author's transl)
Kreutzberger,Schroeders
, p. 994 - 997,995,997 (2007/10/09)
After the conversion of nitrosubstituted aromatic carboxylic acids (3) into the corresponding carboxylic acid chlorides (2), the N-[1-adamantyl]-carboxylic acid amides 4a, 4b, and 4c may be obtained through interaction with 1-amino-adamantane (1). By the same reaction principle,1-adamantyl acetylchloride (6) obtained from 1-adamantyl acetic acid (7) reacts with 2-nitroaniline (5) to give 1-adamantyl-acetic acid-[2-nitroanilide] (8), which may be converted into 2-[1-adamantyl-methyl]-benzimidazole (10) via N-[1-adamantyl-acetyl-]-o-phenylenediamine (9).
