345-81-3Relevant articles and documents
Method for selective N-methylation of secondary amide
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Paragraph 0011, (2019/03/08)
The invention relates to a method for selective N-methylation of secondary amide. The method is characterized in that the secondary amide is in an organic solvent N, N-dimethyl formamide or dimethyl sulfoxide, trifluoroacetic acid methyl ester serves as a methylation reagent, and reaction is performed in the presence of sodium hydride, potassium tert-butoxide or sodium methylate, so as to obtain aselective N-methylated product. The method has the characteristics that generally a trifluoroacetylation product is produced when the trifluoroacetic acid methyl ester is reacted with amine compounds, however a N-methylated product can be selectively obtained when the trifluoroacetic acid methyl ester is reacted with secondary amide; the method is simple to operate, low in cost, mild in reactionconditions and high in selectivity, and avoids the use of hypertoxic methylation reagents, such as dimethyl sulfate and methyl iodide.
Domino Pd0-Catalyzed C(sp3)–H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates
Rocaboy, Ronan,Dailler, David,Zellweger, Florian,Neuburger, Markus,Salomé, Christophe,Clot, Eric,Baudoin, Olivier
, p. 12131 - 12135 (2018/09/11)
The Pd0-catalyzed C(sp3)-H arylation of 2-bromo-N-methylanilides leads to unstable benzazetidine intermediates that rearrange to benzoxazines through 4π electrocyclic ring-opening and 6π electrocyclization. The introduction of a bulky, non-activatable amide group on the nitrogen atom was key to favor the challenging reductive elimination step and disfavor undesired reaction pathways.
Phosphorus in organic synthesis. Acyloxyphosphonium salts as chemoselective acylating reagents
Froyen, Paul
, p. 5359 - 5362 (2007/10/03)
Acyloxytriphenylphosphonium salts 1 prepared in situ react with a variety of aminophenols to give the corresponding amides in excellent yields. At -25°N-acylated products are formed exclusively, whereas 0°some O-acylated products are observed. 1 is also a