Synthesis Of O-aminobenzamides Via Palladium-catalyzed Orthoselective C-H Activation & Carbonylation Of N-substituted Anilines

o-Aminobenzamides have been found wide applications in medicine,pesticides and organic synthesis owing to their significant bioactivities and pharmacological activities.Currently,there are still many drawbacks associated with their synthetic methods in different degrees,such as low atomic economy,serious environmental pollution,severe corrosion of equipment,high cost,and lengthy reaction steps.In this paper,with cheap and easily available N-substituted anilines,CO and amines as the starting materials,the target compounds o-aminobenzamides can be obtained directly via palladium-catalyzed ortho-selective C-H activation & carbonylation of N-substituted anilines.Thus,a new approach to o-aminobenzamides has been developed with high atom economy,friendly environment,mild conditions,low cost,and simple synthesis.This article is divided into four chapters,the details are as follows:Chapter One,literature review.Important applications of o-aminobenzamides in pharmaceutical,pesticide sectors and organic synthesis are introduced.Palladium-catalyzed C(sp~2)-H activation & carbonylation reactions are also reviewed.On this basis,the research topic of this paper is proposed.Chapter Two,synthesis of o-aminobenzamides via palladium-catalyzed ortho-selective C-H activation carbonylation of N-substituted anilines.In this chapter,using N-substituted anilines,carbon monoxide and amine as starting reagents,palladium acetate as catalyst,o-aminobenzamides can be synthesized directly by palladium-catalyzed ortho-selective C-H activation & carbonylation.The factors influencing of the reaction,such as reaction time,reaction temperature,dosage of oxidant species,kinds and amounts of additives and solvents were investigated and optimized.Finally,a series of o-aminobenzamides were synthesized in moderate to good yields under the optimal conditions.Chapter Three,mechanism discussion of palladium-catalyzed ortho-selective C-H activation & carbonylation of N-substituted anilines.According to the experimental results and,literature,the roles of potassium iodide,acetic acid,palladium acetate,acetic acid copper and oxygen have been preliminarily investigated.The plausible mechanism is proposed based on the obtained results.Chapter Four,synthesis of unsymmetrical 1,2,3-thiadiazole urea via selenium-catalyzed carbonylation of 5-amino-1,2,3-thiodiazole and amine.After completing the above research contents,the synthesis of unsymmetrical 1,2,3-thiadiazole ureas via selenium-catalyzed carbonylation of 5-amino-1,2,3-thiodiazole and amines was studied.The optimum reaction conditions were obtained by the optimization of experimental conditions.Finally,a series of unsymmetrical 1,2,3-thiadiazole ureas were prepared in moderate to good yields under the optimal conditions.