Study On The Cleavages Of Inert Aryl C-N Bond Of N-aryl Amides And Synthesis Of Furo[2,3-b] Quinolines

This paper mainly involves the following two aspects of the main contents:(1)Highly Selective Cleavage of Inert Aryl C-N Bond in N-Aryl Amides;(2)Br?nsted Acid-catalyzed the Synthesis of Furo[2,3-b]quinolones.(1)Highly Selective Cleavage of Inert Aryl C-N Bond in N-Aryl AmidesAmide is widely found in natural products,the protein is a natural polymer compound linked by an amide bond.Many alkaloids,such as colchicine,febrifugine and ergocornine,contain amide bonds.There are a number of synthetic methods of primary amides.However,there is no method for the synthesis of a primary amide through an aryl C-N bond cleavage reaction promoted by the hypervalent iodine reagents.Additionally,the aryl group can be stripped as a protecting group for an amide during the reaction process by using this strategy to prepare C-N.In this work,we synthesized the acyl amine compounds at room temperature by adopting IBX as an oxidant and HFIP/H2 O as solvents.The inert C(aryl)-N bond cleavage reaction has the advantages of easy availability of raw materials,good selectivity,highly product yield,good compatibility of functional groups and easy handling of the reaction.(2)Br?nsted acid-catalyzed the Synthesis of Furo[2,3-b]quinolinesFuroquinolines are one of the most important heterocyclic compounds containing nitrogen and oxygen atoms.Alkaloids containing this type of maternal nucleus,such as ?-fagarine and dictamnine,are widely found in Rutaceae plants and have a variety of biological activities,including anti-virus,anti-bacteria,anti-HIV,anti-inflammation,anti-tumor and anti-cytotoxin.Dictamnine is such kind of natural product with the simplest structure of furoquinolines nuclei structure.Therefore,the development of new synthetic furoquinolines compounds still has practical significance and theoretical research value.In this work,we present an approach for the preparing of furo[2,3-b]quinolines with multi-substituted furans as raw material that is simple and readily available and under the promoting of trifluoromethanesulfonic acid along with the Friedel-Crafts reaction.This method has advantages of simple operation,good compatibility of functional groups,effective regional selectivity and relatively high product yield.