637-56-9Relevant articles and documents
Mild N-deacylation of secondary amides by alkylation with organocerium reagents
Wang, Ai-E.,Chang, Zong,Liu, Yong-Peng,Huang, Pei-Qiang
supporting information, p. 1055 - 1058 (2015/09/01)
Secondary amides are a class of highly stable compounds serving as versatile starting materials, intermediates and directing groups (amido groups) in organic synthesis. The direct deacylation of secondary amides to release amines is an important transformation in organic synthesis. Here, we report a protocol for the deacylation of secondary amides and isolation of amines. The method is based on the activation of amides with Tf2O, followed by addition of organocerium reagents, and acidic work-up. The reaction proceeded under mild conditions and afforded the corresponding amines, isolated as their hydrochloride salts, in good yields. In combination with the C-H activation functionalization methodology, the method is applicable to the functionalization of aniline as well as conversion of carboxylic derivatives to functionalized ketones.
A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-Narylacetamides catalyzed by SOCl2
Wang, Gong-Bao,Wang, Lin-Fa,Li, Chao-Zhang,Sun, Jing,Zhou, Guang-Ming,Yang, Da-Cheng
experimental part, p. 77 - 89 (2012/05/20)
Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides. Springer Science+Business Media B.V. 2011.
Comparative Structure-Activity Relationships of Antifolate Triazines Inhibiting Murine Tumor Cells Sensitive and Resistant to Methotrexate
Selassie, Cynthia Dias,Hansch, Corwin,Khwaja, Tasneem A.,Dias, Cecilia B.,Pentecost, Stephanie
, p. 347 - 357 (2007/10/02)
The inhibitory effect of 108 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(substituted-phenyl)-s-triazines on murine L5178Y tumor cells, resistant and sensitive to methotrexate (MTX), has been studied.From the pI50 values, quantitative structure-activity relationships have been formulated which show that the lipophilic triazines are much more inhibitory against resistant cells than methotrexate or hydrophilic triazines.The results are compared with the behavior of other antifolate drugs that have been used in chemotherapy, as well as with eight antitumor drugs that are notantifolates.The acquired resistance of these cells toward hydrophilic antifolates may be attributed to the combined effect of an impaired active-transport system, a change in the conformation of dihydrofolate reductase in the resistant cells, and an amplified production of dihydrofolate reductase in the resistant cells.