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بیست و نهمین کنفرانس شیمی آلی ایران
DFT study on the mechanism of aza-Diels Alder reaction of cyclic and acyclic enamides with 1,2-diaza-1,3-dienes
نویسندگان :
Mahsa Bakhshian ( دانشگاه ازاد بابل ) , Mina Haghdadi ( دانشگاه ازاد بابل )
کلید واژه ها :
Tetrahydropyridazine،DFT study،regioselectivity
چکیده مقاله :
Tetrahydropyridazine rings, as six-membered N-containing heterocyclic blocks, are widespread in many pharmaceutically active molecules and biologically natural compounds.[1] In this regard, the [4+2] cycloaddition reaction of 1,2-diaza-1,3-dienes and various alkenes would be a straightforward approach for the construction of 1,4,5,6-tetrahydropyridazine skeletons. In 2021 Shen et al. reported some aza-Diels−Alder reactions of enamides with 1,2-diaza-1,3-dienes, which successfully formed a wide range of fused polycyclic tetrahydropyridazines. [2] Herein, we investigated the mechanistic details of these reactions through computational analysis by the DFT method. It was found that, enamides applied as electron-rich participants and irrespective of locality, electronic property, and number of the substituents could be suitable for the inverse electron-demand [4+2] cycloaddition reaction. Moreover, regardless of electron-withdrawing or electron-donating group on the aryl ring (Ar) of acyclic enamides, did not have significant influence on the reactivity. All of cycloaddition reactions are completely regioselective and take place via a polar and asynchronous process. Analysis of the reactivity indices shows that 1,2-diaza-1,3-dienes present a strong electrophilic character and enamides have a strong nucleophilic character.
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