Fe（NO₃）₃-promoted The Cyclization Of β,γ-unsaturated Oximes And Iodine-catalyzed The C3 Alkylation Of Indoles With 1,3,5-triazines

Nitrate compounds have extremely important applications in the field of organic chemistry synthesis.It has attracted the attention of organic researchers for developing synthetic methods to efficiently introduce nitrate functional groups.Therefore,many researchers have successively reported on the synthetic methods of nitrate compounds.In the reported methods,most of the nitrate compounds are synthesized by nitrate,nitric acid and metal nitrates,while the research on the synthesis of nitrate compounds with Fe（NO₃）₃·9H₂O as the source of nitrate functional group is rare.In this paper,we report a green,economical and efficient Fe（NO₃）₃-promoted radical cyclization addition reaction ofβ,γ-unsaturated oximes.With the Fe（NO₃）₃·9H₂O both acting as the accelerator and nitrate ester group source,theβ,γ-unsaturated oxime radical cyclization addition reaction was realized,and incorporated the nitrate ester group functional group into the olefin.This cyclization reaction enable the synthesis of various isoxazoline derivatives containing nitrate ester functional groups in high yield and high regioselectivity.The reaction system has excellent group tolerance.The easy conversion of cyclization products were achieved,which readily afford the isoxazoline compounds containing groups,such as I,N₃,OAc,and OH.Indole and its derivatives have been widely used in the fields of pharmacy and agricultural chemistry.Increasing attention was focused on the the development of new organic synthetic chemical reaction involving indole.In particular,the electron-rich C3of indole can introduce many kinds of function group.In addition,from the reported literature,it is known that 1,3,5-triazine as a typical nitrogen-containing six-membered ring compound,can undergo ring expansion and aminomethylation reactions in organic synthesis reactions.However,the alkylation reaction by using 1,3,5-triazine to synthesize compounds having NH₂ unit has not been reported yet.In this paper,we will report a C3-alkylation reaction of indole with 1,3,5-triazine by iodine catalysis,which can generate a series of indole compounds containing NH₂.Of particularly note,The I₂-catalyzed alkylation method avoids the use of any transition metal catalysts and oxidants,forming the desired products in good to excellent yields.