Abstract
N-Tosyl-2-nitropirrole and N-Tosyl-3-nitropirrole reacts with poorly and activated dienes using protic ionic liquids as reaction media. They exhibit a dienophile character producing the corresponding indoles through a Diels-Alder process. In all cases the presence of protic ionic liquids as reaction media improve the yields respect to use of molecular solvent, while the temperature and the reaction time decrease.
Highlights
The Diels-Alder (D-A) reaction is one of the most useful processes in preparative organic chemistry
Due to our interest in the cycloaddition chemistry of substituted aromatic heterocycles with electronwithdrawing groups, we have reported that N-tosyl-2- and 3-nitropyrroles react as electrophile in normal electron demand D-A reactions.[2]
Considering the results obtained in these thermal polar D-A reactions using molecular solvents as reaction media, the purpose of this work is to analyze the influence of room temperature ionic liquids (RTILs) in polar cycloaddition reactions in which the electrophiles are relatively poor
Summary
The Diels-Alder (D-A) reaction is one of the most useful processes in preparative organic chemistry. It is worth noting that these variants exist in the substitution of the reaction component and in the electronic nature of these dienes and dienophiles.[1] Due to our interest in the cycloaddition chemistry of substituted aromatic heterocycles with electronwithdrawing groups, we have reported that N-tosyl-2- and 3-nitropyrroles react as electrophile in normal electron demand D-A reactions.[2]
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