117111-00-9Relevant academic research and scientific papers
Hetero-Diels-Alder reactions of novel 3-triazolyl-nitrosoalkenes as an approach to functionalized 1,2,3-triazoles with antibacterial profile
Lopes, Susana M.M.,Novais, Juliana S.,Costa, Dora C.S.,Castro, Helena C.,Figueiredo, Agnes Marie S.,Ferreira, Vitor F.,Pinho e Melo, Teresa M.V.D.,da Silva, Fernando de Carvalho
, p. 1010 - 1020 (2018)
The generation and reactivity of 3-triazolyl-nitrosoalkenes are reported for the first time. The study showed that hetero-Diels-Alder reaction of these heterodienes is an interesting synthetic strategy to functionalized 1,2,3-triazoles, including 1,2,3-tr
Metal-Free Route for the Synthesis of 4-Acyl-1,2,3-Triazoles from Readily Available Building Blocks
Thomas, Joice,Goyvaerts, Vince,Liekens, Sandra,Dehaen, Wim
supporting information, p. 9966 - 9970 (2016/07/19)
Functionalized 1,2,3-triazole heterocycles have been known for a long time and hold an extraordinary potential in diverse research areas ranging from medicinal chemistry to material science. However, the scope of therapeutically important 1-substituted 4-acyl-1H-1,2,3-triazoles is much less explored, probably due to the lack of synthetic methodologies of good scope and practicality. Here, we describe a practical and efficient one-pot multicomponent reaction for the synthesis of α-ketotriazoles from readily available building blocks such as methyl ketones, N,N-dimethylformamide dimethyl acetal, and organic azides with 100 % regioselectivity. This reaction is enabled by the in situ formation of an enaminone intermediate followed by its 1,3-dipolar cycloaddition reaction with an organic azide. We effectively utilized the developed strategy for the derivatization of various heterocycles and natural products, a protocol which is difficult or impossible to realize by other means.
Microwave enhancement of a 'one-pot' tandem azidation-'click' cycloaddition of anilines
Moorhouse, Adam D.,Moses, John E.
scheme or table, p. 2089 - 2092 (2009/04/07)
The practical and efficient one-pot azidation of anilines with the reagent combination t-BuONO and TMSN3 has become a useful addition to the click-chemistry toolbox. Herein we report a modification of this methodology, using microwave radiation
Intermolecular Thermal Reaction of Arylnitrenes with Furans
Benati, Luisa,Montevecchi, Pier Carlo,Toselli, Maurizio,Spagnolo, Piero
, p. 1859 - 1864 (2007/10/02)
4-Methoxy-, 4-chloro-, and 4-nitro-phenylnitrenes have been thermally generated by decomposition of the corresponding aryl azides in the presence of furan and a series of 2-substituted and 2,5-disubstituted furans. 4-Nitrophenylnitrene has been shown to be capable of undergoing electrophilic addition to the furan ring both at the α- and β-position, whereas only evidence of α-attack has been provided by 4-chlorophenylnitrene.On the other hand, no evidence of electrophilic attack has been obtained with 4-methoxyphenylnitrene, which affords only products ascribable to the triplet nitrene.The formation of a number of products ultimately resulting from nitrene attack at the α-position of the furan ring followed by a ring-opening process and the general occurrence of 1-(4-nitrophenyl)- and 1-(4-chlorophenyl)-1,2,3-triazole from thermolysis of 4-nitro- or 4-chloro-phenyl azide in the presence of the furans examined is discussed.
