Study On The ‘One Pot’ Sulfonylation And Chlorination Of 2-Arylquinoline N-oxides Under Metal-free Conditions

In this thesis, ‘one pot’ sulfonylation and chlorination of 2-arylquinoline N-oxides under metal-free conditions are studied The main results obtained are as follows:Sulfone skeletons have been widely used as the key compounds applied in numerous total syntheses,It exists extensively in pharmaceutical molecules,natural products and so on. There are some disadvantages with the traditional procedures to building such a structure, such as narrow scope of substrates and hash reaction conditions., In addition,arylhaldies are important intermediates product in industrial production, Taxic POX3 or PX5 provided halogen source in the literature. Transition-metal-catalyzed synthesis hetero aryl sulfones and arylhaldies were report in recent years Quinoline N-oxides are used to synthesis complex molexules by C2-H and C8-H bond cleavage however, C3-H and C4-H bond cleavage is rarely reported.Aryl sulfonyl chloride is a versatility substrate for sulfonylation and arylation to to form C-S、C-C independently. Howerer, to the best of our knowledge, there is no report to serve aryl-sulfonyl chloride to for chlorination and sulfonylation in one pot. Herein, we disclose a highly practical procedure to build 3-sulfonyl 2-arylquinoline N-oxides and 4-chloro- 2-arylquinoline simultaneously.(Scheme 1) This protocol features a simple system, highly atomic economy efficiency. environmental friendliness, under additives and base free conditions. On the basis of controlled experiments and literature, a plausible reaction mechanism was proposed and shown in Scheme 2.